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Dear Captain Awkward,

My group of friends and I are all in our 30s, mostly queer, and have found ourselves in widely different circumstances regarding: financial stability, disability, and cultural acceptance. Most of this friend group has known each other for 10+ years. We’re pretty close! We share a lot of solidarity and a history of caring for one another. But, recently, our group has been fracturing around issues of, well…privilege.

This seems to happen in two distinct ways. The first and most obvious is when friends with certain privileges (relative health, wealth, visa status, or social acceptance of their queerness in their community) constantly, cluelessly brag. In a truly tone-deaf, “please read the room” way. 

Microaggression Example #1: Empathy? Interrupted.

The friend group is talking about housing insecurity. Specifically, we’re comforting and troubleshooting with a friend who is dealing with an unexpected eviction notice. Suddenly, a different friend starts talking about how she just bought a house! She’s “relieved” because finally got a house (after previous bids fell through). She’s “tentatively excited” and going to throw a lavish housewarming party! She’s “not sure” if she’s going to be able to invite all of us to her party, or when it will be, but she just wants us to be happy with her.

To be clear, she wasn’t bringing this up to offer to help the friend facing urgent eviction, or anyone else’s ongoing issues with housing insecurity. She just literally abruptly changed the subject to brag about her good luck. Like, she was officially done with empathizing with our other friend. And, that’s how she decided to show it. My impulse at that moment was to say, “Hey, if you’re not going to help or empathize, don’t say anything! Nobody asked you to talk. Not everything is about you. We’re trying to solve a problem. If you’re not, fine, but then just wait a bit.”

To be clear, I did not act on this impulse!

Obviously, I know challenging my friend like that would be rude and unhelpful. But, everyone was just awkward silence or vaguely kinda…agreeing that it was good? 

And saying nothing made me feel pretty awful.

I regret not standing up for my friend in crisis, whose conversation got derailed. I know, were situations reversed, I would want someone to stand up for me, to emphasize that requesting empathy and help is not burdensome or shameful, and that the derailing friend’s reaction was an outlier. 

But, like everyone else in the group, I said nothing. 

If it was just this one time, it wouldn’t be a big deal. But the pattern is clear with more than one friend in the group: A friend is seeking empathy or practical help (or both) and a different friend decides to change the conversation to a more “positive” topic: bragging about their privileges. 

This even happens in group chats. Where you can easily just step away from a conversation that doesn’t interest you! 

The other, more subtle way this plays out is with a refusal to accommodate marginalized friends. In particular, this has increasingly happened whenever we try to make plans to hang out. 

Microaggression Example #2: Exclusion, Uncompromised

-Friend A suggests going to a specific concert venue (say, “Staircase World,”) to catch Local Band. 

-Friend B mentions Staircase World is not wheelchair accessible, and they weren’t able to enter the last time they tried to go. They recommended catching a different show in a different location, which is accessible. 

– Friend C mentions liking the band Friend B recommended, and also brings up a few other events in more accessible locations 

– Friend A is annoyed and says they only want to go to see Local Band at Staircase World, and they’re going regardless of whether anyone else joins

– Friend D says maybe we could split into two groups, go to different shows, and all meet up later [Note: I am Friend D in this scenario]

– Friend A says they don’t think they’ll be up for meeting anywhere afterward, they don’t like being up too late

– Friend C gets annoyed and says, “Why is seeing Local Band at the notoriously ableist Staircase World more important than spending time with the people you care about? You seriously won’t even consider a compromise like leaving a little early to hang out altogether before it’s too late?”

Aaaand obviously. Obviously! Friend C said the wrong thing. In isolation, it is an overreaction. 

But it. Keeps. Happening. 

It seems like every conversation now! 

Friend A is mad at Friend C for losing her cool and for being “judgmental”. Friend C and B are both mad at / hurt by Friend A’s willingness to exclude them so casually due to their disabilities. 

Everyone in the group seemed to pick a side, and I kinda ended up on B & C’s side. But, really I’m Team Compromise! The weekend came and went, and the friend group seems ok.

But I also feel like, on some level, I’m just holding my breath waiting for the next clueless privileged comment or exclusionary take to shatter the group entirely. 

Sometimes, it’s disability access. Sometimes it’s a financial barrier, and refusal to consider an affordable alternative (nor pitch in to pay for a low/no income friend’s ticket). 

Is there any way, at all, to persuade the more privileged friends to stop dropping micro-aggressive grenades in our conversations?

I love my friends! I love and care about and deeply admire all of them. 

Maybe it’s the middle child in me, but I really want to negotiate a peace here. Maybe I could have a big-picture conversation with a few of my friends about this. I truly believe we can all make peace and take care of each other.

Heck, we can even celebrate the random good luck in people’s lives! Getting a house and getting to travel to Europe are all positive events worth celebrating. It’s just a timing issue of when these events are brought up in conversation, mostly. 

Likewise, I don’t think the friends who keep suggesting exclusionary hangouts are doing it on purpose. Are there any scripts you think could work here? Either “big picture” conversations, or in-the-moment statements. I’m hoping for scripts that are polite, yet effectively prevent derailment away from empathy. Or, scripts to effectively re-center inclusion and equity in conversations about hanging out. 

Or both?

Also, do you think there’s anything I should say to the friends who have been subject to exclusion or empathy rejection? Should I try to help them see the perspective of the more privileged friends in some way? Or, is that disrespectful and just going to make things worse? 

Sincerely,

Stuck Diplomat, Seeking Scripts

Dear Stuck Diplomat,

People often call me diplomatic, and it’s true, but not in the way they mean. Diplomacy isn’t just about being good at de-escalation, peace-keeping, compromise, or finding palatable ways to deliver hard truths. Diplomacy is about understanding power and leveraging what power you have in negotiations, which sometimes includes strategically escalating conflicts or letting them play out. You most likely don’t have the power to fix your friends’ hearts or make your group chats all run smooth, and I don’t have any magic scripts up my sleeve that will guarantee that you can, but it doesn’t mean you have no power in the situation. It’s there, just, I suspect that it’s not where you’re looking for it.

Let’s dig into your examples and see if there is another way to handle stuff like this in the future. You write:

My impulse at that moment was to say, “Hey, if you’re not going to help or empathize, don’t say anything! Nobody asked you to talk. Not everything is about you. We’re trying to solve a problem. If you’re not, fine, but then just wait a bit.”

Obviously, I know challenging my friend like that would be rude and unhelpful.

…And saying nothing made me feel pretty awful.

…I regret not standing up for my friend in crisis.…But, like everyone else in the group, I said nothing.

Which is worse, risking a full-blown argument by speaking up about bad behavior in the moment, or how bad it feels to not have spoken up at all? Would it really have been the end of the world if you’d just said what was on the tip of your tongue?

There’s this persistent idea that the *only* right way to respond to shitty interpersonal behavior is to empathize deeply with the shitty person, figure out precisely why they are being like that, and use your own compassion to create a teachable moment that fosters greater self-awareness that results in eventual behavioral change from the inside out, and anything less constitutes a failure of *your* patience & empathy. That’s where the notion that saying any version of “Hey, can you knock it off right now with the housewarming party planning?” would be “rude” and “unhelpful” comes from. If somebody’s being Rude, you’re supposed to Polite at them so hard that they Learn An Important Lesson, Eventually.

A couple problems with that:

1. What good does this do for the targets of shitty behavior?
2. What happens if the shitty people never learn?
3. What happens if they learn, but it’s exactly the wrong lesson? “I can be as shitty as I want, and people must be polite to me at all costs, and if they fail to tolerate my bad behavior with perfect grace, it makes them even worse than me and everything becomes actually their fault? Sweet!”
4. What do you win if you successfully erase your anger and annoyance from all of your closest friendships and present only the most accommodating, peace-making parts of yourself?

The answer to #1 is “nothing much” and the answer to #2-#4 about what happens and what you “win” is More Shitty Behavior, All The Time, Basically Forever because you’ve robbed yourself of the tools for actually addressing it, tools like, “healthy expressions of authentic emotions” and “meaningful consequences.”

My pitch to you is basically, what if we changed the order of operations for dealing with someone whose behavior is out of pocket? What if we administered consequences first, and let the epiphanies sort themselves out later? If people get rapid negative feedback every time they do or say something shitty, maybe they’ll learn to think and feel differently over time, but that slow internal work is none of your business. If people wanna be assholes, they’ll need to do it somewhere else. If they want to hang out with you, there are limits on acceptable behavior.

One benefit of this approach is that you don’t have to figure out someone’s entire deal or manage the feelings of every bystander and mutual acquaintance before you get to do something about shit that bothers you. “Let’s have one deep emotionally difficult discussion where I recount your crimes for the entire time we’ve known each other and hopefully persuade you change your entire personality” gets replaced with “Whoa, that was not cool!” Another benefit is that the other targets of shitty behavior don’t have to decide if your invisible dismay is really invisible enabling of their bullies.

To pull that off, you have to stand in your own integrity –which includes your anger sometimes–and let that be enough to drive your words and actions. It’s not “oh my god, how might this tone-deaf behavior be affecting my friends who are in crisis” in the abstract or “oh my god, does house-buying friend even realize how she is coming across right now, I’m so embarrassed for her” while you quietly cringe and empathize and try to brainstorm a perfect way to make none of this have ever happened. You put in all this time empathizing and worrying, but it didn’t change anything. Time to simplify: How did your friend’s aggressive non-sequiturs affect you? Did you like it and want her to talk about her new house more or did you want her to stop? The leveling up happens when you decide, “as an equal participant in this conversation, I want to talk about eviction solutions, not housewarming plans right now, so that’s what’s I’m gonna do.”

Script-wise, that could look like a lot of things:

• Change the topic back. “Interesting, we’ll have to catch up later and you can tell me all about the new place. Anyway, back to what we were discussing. About-To-Be-Evicted Friend, sorry, please continue. What do you think you’ll do and how can we help?”
• If necessary, do it as as side-conversation with the person you’d rather be talking to. “Hey, sorry we got interrupted, that was really awkward. Are you good? Where were we?” 
• If words escape you,  make eye contact with the oblivious friend and do the universal “Shut It Down!” gesture. 
• If you don’t want to call her out in public, pull her aside. “Yo, I’m happy for your new house and all, but this seems like not the right moment. Can you and I make time later and you can catch me up all about housewarming plans, etc. then?”
• Or follow up and have it out the next day. “Hey, last night, when it felt like nobody was celebrating with you about your new house and it got kinda awkward? Yeah, maybe you noticed we were in the middle of a conversation about looming eviction? I get wanting us to be happy for you, and I am happy, but interrupting a conversation about impending homelessness to demand that we celebrate climbing the property ladder with you right then was beyond tone-deaf.”

None of that is gonna be comfortable to execute, but exactly none of it is ruder than whatever she was doing. Maybe your friend would have gotten the message, apologized, and acted right. Maybe it would have turned into a giant argument. You may be right that speaking up would only have derailed everything further, but I want you to keep in mind that silent dismay and silent agreement look identical from the outside. You know for a fact that saying nothing feels awful and does nothing to curb the behavior you dislike, so what do you want to do about that next time? 

The more you let go of managing other people’s reactions and speak up for yourself and only for yourself, the more power your words will have. Not “Everybody wishes you wouldn’t say stuff like that in the group chat” or “Crisis-Friend might be offended, I’m just trying to look out and be sensitive to that.” You were there, you were annoyed, that’s good enough! Stick with “I don’t appreciate the interruption, I want to keep talking about housing logistics until the issue is resolved, but why don’t I call you tomorrow and you can tell me all about New House then.”

Let’s apply this to your other example. Accessibility is a fraught issue, and COVID-19–WHICH IS TOTALLY STILL A THING BTW– hadn’t even entered this particular chat, but what you’re really describing is people making two completely different sets of plans and asserting multiple value systems, anxieties, and boundaries all at once.

• “It’s okay to want to do my own thing once in a while, and I’m not going to the concert AT you.”
• “I don’t go to inaccessible venues, so if we’re gonna do a group thing it needs to be somewhere else.”
• “You wanting to skip a group hangout to do your own thing makes me feel rejected and sad.”
• “I don’t care where we go, but conflict is scary and bad. Can’t we just get along?”
• “Public venues should be accessible to all, and we must demonstrate solidarity with disabled people by boycotting inaccessible spaces.” .
• “If by ‘we’ you mean ‘you,’ totally! But actually I want to go to the concert bad enough that I’m willing to risk going alone and making you mad.”
• “Compromise! (Drinks later?)”
• “No drinks for me, thanks!”

Is this a fight about disability justice and fairness, a fight about friendship, or a fight about varying preferences? Having all three at once doesn’t seem to be working out. The Geek Social Fallacies are running rampant here, most notably #2 , “Friends Accept Me As I Am” (and as a result never, ever criticize each other) and #5: “Friends Do Everything Together.” People’s circumstances and priorities often change a lot between their 20s and 30s, and some or all of you might be outgrowing the way things have always been done but not yet sure what happens next. “We’ve been through a lot together” isn’t the same as “We enjoy each other’s company, present tense” or “Let’s do everything together forever and always” or “I’m willing to pay so that we can all keep doing stuff together always” and what you’re witnessing might be natural growing pains as people drift apart or realize they are less compatible than they once were. Plus, some shit is just awkward no matter how you slice it. Housing insecurity, income inequality, and ableism are definitely in the pile of things that it’s hard to talk about in a way where everybody feels awesome all the time.

You write: 

Friend A is mad at Friend C for losing her cool and for being “judgmental”. Friend C and B are both mad at / hurt by Friend A’s willingness to exclude them so casually due to their disabilities. 

Everyone in the group seemed to pick a side, and I kinda ended up on B & C’s side. But, really I’m Team Compromise! The weekend came and went, and the friend group seems ok.

What I’m reading is that the friend group survived an awkward argument plus one person going off and doing their own thing for a single night. Your suggested compromise was fine, just, not everybody wanted to do the same stuff. What is there for you to manage or fix here? It seems like the necessary skill-building is not finding a perfect script, it’s more about learning to sit with discomfort and conflict without trying to smooth it over all the time. Here are a few strategies that might not cure anything but are unlikely to worsen anything that’s already bad: :

• Stop managing other people’s feelings about each other. Especially don’t minimize, manage, or police your friends’ anger at each other. Maybe A and B/C will stay peeved for a while. Maybe that was also a necessary argument they needed to get out of their systems!
• You get to mute the group chat or bow out of in-person conversations that annoy you, especially if you’re having a hard time disengaging from other people’s fights. “I’m gonna stretch my legs. My vote is that we do X, but I’m fine with whatever, just let me know when you decide.” It’s easier to manage your exposure and proximity relative to your own stress levels and bandwidth than it is to convince all of them to be different.
• When you’re in charge of planning events for this group, you get to plan stuff your way, with the cost and accessibility features you desire. If other people plan differently, maybe stop trying to compromise or manage group dynamics and guest lists and think in terms of “Do I personally want to opt in or out of whatever this person is inviting me to?” If you opt in, show up and have a good time with whoever is there without making it about who didn’t come. If you opt out, your responsibility for how it all goes is zero.
• Is it time for you to plan more frequent 1:1 hangouts or smaller group things and not try to cross all these streams all the time? What if you took a break for the rest of the year and saved getting the whole group together for a few special occasions? Would you all like each other more if you saw each other slightly less?
• It sounds like maybe some people in the group are sick of picking up the tab or only doing free-ish stuff but they don’t want to say that outright, others are sick of being poor and tired of having to hold their hand out, nobody is talking about it directly, and thus it’s an awkward guessing game every single time you try to make plans.Take the guessing out of it! Like, stop hinting, stop quietly judging, stop trying to get people to offer, and just ask the people with money to do what you want them to do when you want them to do it. That way they can say yes or no and everyone will have the information they need to make good decisions.
• If you’re someone with both more relative privilege and more relative awareness of inequities, then you can afford be very boring and consistent about money. “Admission cost for that is $X, if four of us split six tickets to cover E and F that comes to $Y/each. Is that cool with everyone? Once you confirm I’ll reserve the tickets.”
• If others are not willing to cover costs for fellow group members for more expensive plans, are you willing & able to throw down the cash yourself? Are you committed stick to only cheap or free alternatives forever, even if it means not everyone will want to go to everything? You get to decide that for yourself, but not for everyone else.
• You can be very boring and consistent about money in the other direction. “That sounds fun, but it’s not in my budget right now. Enjoy!” “Can we do something free or cheap this time?” “I can throw in exactly $10. Are you okay covering the rest, or should we just plan something else another time?”
• Right now you’re doing a lot of mental work about all of this without getting any of the results you want. What if you did…less? Consider a rule for yourself where if something annoys or upsets you, you’ve got 24 hours to either say something about it out loud to someone who can do something about it or let it go.
• Is it time to remind you one last time that all of these people have the same agency you do to run their friendships however they want and budget their time and money in whatever way works best for them? That includes the financially-strapped members of the group.

That’s what I’ve got, sorry that it’s not what you were hoping for. I strongly believe that your best chance of holding onto these important friendships is to remove pressure and let go of the idea of One Big Group, Together Always, with you as its savior, peacemaker, or asshole-whisperer-in-chief.

Dear Captain Awkward,

I find myself in a rather delicate predicament involving my neighbors—the couple who live a few houses down—and I need your guidance. As someone with an insatiable curiosity and a knack for picking up on the smallest details, I’ve noticed some rather intriguing developments in their lives that I feel compelled to address.

The wife, a dynamic and ever-energetic woman, is always the life of the neighborhood. She’s constantly orchestrating events, from extravagant dinner parties to spontaneous weekend getaways. Her enthusiasm is undeniably infectious, but it seems to be having an unexpected impact on her husband. I’ve observed him looking increasingly disheveled and somewhat out of place at these events, particularly in the designer outfits she insists he wear. The poor man seems so uncomfortable, often shifting awkwardly or fidgeting with his collar.

Here’s where it gets a bit more personal: I’ve seen him at the local coffee shop, visibly stressed, and on one occasion, he even mentioned to a mutual acquaintance how he feels overwhelmed by the pressure to conform to her lavish lifestyle. I couldn’t help but overhear this conversation while I was waiting in line, and it broke my heart to see him so distressed. It’s clear he longs for a simpler life, yet he’s caught in a whirlwind of her high expectations.

In addition, I’ve noticed subtle hints of tension at their home, like the way he hesitates before answering her calls or the strained smiles they exchange when they think no one is watching. I feel it’s my duty to step in and offer my perspective. My communication skills are top-notch, and I’ve got a real talent for resolving conflicts and suggesting improvements. It seems only right that I share my thoughts on how they might find a better balance between her vibrant, high-energy world and his more relaxed, introspective nature.

I’ve been considering a friendly visit to share my observations, perhaps over a cup of tea. I could gently suggest that she might consider his comfort more, and offer some advice on how they could adjust their lifestyle to better accommodate his needs. I genuinely believe this would help them strengthen their relationship and bring them closer together. Of course, I’d approach it in the most tactful and considerate way possible—after all, my intention is to be helpful, not intrusive.

Am I crossing a line by contemplating this? I genuinely want what’s best for them and think my unique perspective could offer valuable insight. Should I go ahead with my plan, or is it best to stay out of their personal matters? I’m torn between my desire to help and my awareness of potential boundaries.

Thank you for sending in the Rear Window remake starring Rachel Lynde I didn’t know I needed.

While I am also a passionate observer of the human condition, and frankly fascinated to know what your advice to these people would even be and how you envision the scene where you deliver it unfolding –does your version end with the couple forming a trauma bond about how weird & terrifying it is to realize that their neighbor has been watching them all this time that does ironically bring them closer together than ever?– this is where I tell you to stop. Please, do not ring these people’s doorbell and offer them unsolicited marital advice based on months of careful observation and coffee-shop eavesdropping. Do not do it over tea, do not do it by the sea, do not do it over Zoom, do not do it in a room. Even if you are right about what you observe (big if), even if your intentions are of the purest, most helpful grade, trust that people mostly do not want you to be smart at them or right about them from afar or show up on their doorstep like an avenging management consultant to troubleshoot stuff that’s none of your beeswax.

If this couple wants a marriage counselor, they can hire one, preferably someone who is bound by a set of professional ethics and who doesn’t live on the block. They are also free to reach out to their local clergy, family members, bartenders, hairdressers, individual therapists, a myriad of hotlines, advice subreddits, and online fora, and their actual close friends for support at any time. Consider that they might already be doing any or all of these things without informing you. Please also consider that what you are oh-so-carefully observing might be a minor mismatch in extrovert-introvert tendencies that they’ve just chosen to roll with because they like everything else about being married to each other.

By contrast, if the husband wanted your advice, you would know without a doubt because he would have asked you. You’d be among the buddies he vents to at coffee shops and not the virtual stranger craning their neck from the barista line and furiously jotting another entry in the Notes app. If you knew him well at all (I mean, to talk to, not just to peer at while he fumbles worryingly with his fancy necktie at parties across the way) then you would have gone up to him that day and said something. Anything. “Hello!” “How are you?” “Yes, it’s me, your neighbor!” “I couldn’t help overhearing just now, and feel free to tell me off if it’s none of my business, but is everything okay?” “Are you looking for advice or are you just venting?”

To be absolutely clear, I am not advising you to strike up a friendship as a means to the end of helping these people figure out their marriage. You are already way too invested in people who are not reciprocally invested in you for that to ever be a good idea. My advice is to stop watching them, stop eavesdropping on them, stop speculating about their marriage, and do literally nothing to insert yourself further into their lives. Say a pleasant hello when you run into them in the neighborhood, and then disengage. If you’re hungry for connection and the opportunity to be useful, maybe find someplace to volunteer in your community and channel your helpful impulses into help that people asked for. Then perhaps this story can remain a comedy and not the opening act of a thriller.

Time for the periodic feature where we treat search strings that brought people here as if they are questions. After this musical interlude, settle in for some snap judgments + no context = assumption theater!

“Flirty answer to what are you doing this weekend.”

I am Captain Awkward, not Major Rizz, but maybe try something like, “I don’t know yet. Why, got a suggestion?”

If the person was trying to feel you out about availability for a date, that gives them plenty of opening to ask you out, and if they weren’t then you haven’t said anything to make it more weird or anything that requires you to do more work about it.

“How to politely tell people I am unemployed.”

Telling the truth about your actual life is not rude, so this is more about what you’re comfortable sharing given the audience and the occasion. You do not owe anyone a version of your life story that meets their expectations, nor do you have to justify or explain your circumstances! If unemployment is a stressful topic for you, I suggest finding the shortest true thing you can say about it and then changing the subject to something you’d rather talk about.

Let’s frame this as ways you could answer a routine “small talk” question from someone you just met: “So, what do you do?”

• “I’m a [profession] by training, but I’m between jobs at the moment. Howabout yourself?”
• “I just graduated and am looking for work as a [job]. And you?”
• “I’m taking some time off at the moment to [take care of family][deal with some medical stuff][finally pursue my dream of sailing around the world on a tiny raft]. What keeps you busy when you’re not working?”
• “Disability keeps me out of the workforce just now, but when I can [I take classes in ______][work on my ______hobby]. What are you nerdy about lately?”
• “Oof, sadly I was just laid off and I’m still figuring out my next move. Did I hear correctly that you’re an art restorer? That’s so interesting, how did you get into that line of work?”

I firmly believe that most people you meet in passing do not have some deep hidden agenda when they ask this question. They do not want to pry deeply into your life, judge you, or make you feel uncomfortable, and they will take their cue from you about how to respond. If you are calm and matter-of-fact in your answers, they will be matter-of-fact in return. If you seem sensitive and raw, they will be sympathetic and apologize for unwittingly poking a sore spot. If you change the subject away from your employment situation and toward something about them, they will let it stay changed. And if they truly want to help, they will a) ask and b) offer concrete solutions that might actually help. “If I hear of any openings that might be a good fit for you, would you like me to pass them along?” “I have some friends in that line of work, would you like me to make an introduction?”

That doesn’t mean that you’ll never run into nosy people, ableist people, “helpful” people who assume that any admission of less-than-ideal circumstances is an invitation to shower you with vintage job hunting tips from the summer of ’68 (when apparently people could guarantee themselves a job by showing up to companies in person out of the blue and calling them nonstop to demonstrate something called “grit” and “persistence.”) Someone who behaves like that isn’t doing it because you did something rude when you answered them truthfully about your life, and you’re not doing anything rude if you develop a sudden need to be elsewhere. “So nice meeting you!”

“How to ask my friends to set me up.”

“Do you know any cool single people you’d be willing to set me up with?”

“Is your friend _______ single by chance? I really liked talking to them when we met. Would you be willing to pass them my info or make an introduction?”

“If I threw a matchmaking party and asked everyone to bring their coolest single friend, would you come and who would you bring?”

They’ll either say yes or no and you can take it from there. And here is my pro-est of pro tips: If your friends say no to setting you up or seem reluctant, and you ask them why, and they’re kind enough to be honest with you, and you argue with their answers, THAT is the why. They want you to be happy, but they don’t want to be blamed for your dating disasters or subject their other friends to whatever that was.

“Why do I feel like I am cheating on my best friend when I hang out with other friends?”

I cannot divine your feelings, I can only offer clarifying questions.

Is the pressure internal or external? In other words, does your best friend do or say stuff that indicates that they might be jealous of when you spend time with other friends, or is that feeling something you’re generating on your own? Are you jealous when your best friend does social stuff without you?

Does whatever this is feel more like a problem or more like an opportunity? If it’s a problem, what would solve the problem, and do you want to actually do whatever that is? Does the prospect of talking about what’s happening with your friend make you feel more excited-nervous or annoyed-nervous?

There’s a lot of open ground on the spectrum between “I might have a little crush on my best friend (or vice-versa)” vs. “Life can be hectic and my best friend and I could probably use more quality time together” vs. “My best friend makes me feel smothered and guilty when I try to spend time with others.” Do any of those possibilities sound more plausible than the others? In a perfect world where this friendship unfolds exactly how you wish it would, what does that look like for you?

“Neighbors pretending to like you when they don’t.” + “Neighbors don’t answer their door only nice when they want something.”

Both of these came in back to back with neighbors misspelled the same way (neibours) so I’m gonna treat them as one. What I’m sensing here is that these neighbors do not want to be friends. They are superficially pleasant, not consistently friendly, and they definitely don’t want you to drop by without warning. It’s understandable if a mismatch in perceived friendliness vs. consistent behavior hurt your feelings or led to confusion, but now you know that whatever is happening right now is as close as you’re ever likely to be. So what do you want to do about it? You always have the option to remain superficially pleasant, avoid dropping in on them or inviting them to hang out, and seek close friendships elsewhere. Don’t confide in them about your personal life or pry into theirs, and don’t center them in your plans. If they seek you out when they want something, feel free to say no to anything that’s annoying or inconvenient for you. But also, feel free to approach them whenever you need something specific and concrete. Transactional, superficially pleasant relationships with people you don’t want to be besties with can be fine, actually, as long as everyone keeps their expectations realistic.

“Is it reasonable for my husband to leave me if he hates my hairstyle?”

There are a few distinct possibilities here:

1. The hairstyle was an excuse for something he was planning to do anyway.
2. He’s a controlling ass who thinks he has authority over your grooming decisions.
3. You did something to your hair that’s so offensive or ridiculous that it’s making him question all of his life choices and everything he knows about you as a person. (This is highly unlikely, but I’ve seen enough white people with corn rows or racist symbols shaved into their hair that I can’t completely exclude the possibility.)

All of these possibilities lead to the same place, in that somebody who would leave you over a hairstyle is someone who would leave you over a hairstyle. Whether you accept or agree with his reasons, he’s gone. Someday both of you can tell the story called “I Can’t Believe I Got Divorced Because of Hair,” and time will tell whether it’s a funny story or the one where you dodged a bullet.

“How to message ‘I am not the right guy for you.'”

If this is a breakup or a “no thanks, I’m not interested in pursuing anything” situation, I would suggest avoiding that angle entirely and replacing it with something more like “I’m so sorry, but I don’t want that kind of relationship with you.” 

It’s not your job to convince other people about what is right for them, it’s your job to decide what’s right for you and act according to your own values and priorities. By pitching it as “I’m not the right guy for you,” you’re trying to let the other person down easy by selling them on the idea that what’s right for you is what’s right for everyone, but what you’re really doing is saying “Your feelings are incorrect.” That potentially puts them in the position of trying to convince you that you are the right person and defending their own wants during a painful moment of rejection. Whether or not they think you are right for them, they are not right for you.Try something like this instead:

• “I’m so sorry, but I know this is the right decision for me.”
• “I just don’t feel the same way.”
• “I wish I shared your feelings, but I don’t.”
• “I’ve decided to break up.”
• “My feelings have changed, and I’m ending the relationship.”

We’re so culturally allergic to direct communication about feelings, so I understand if those seem harsh in comparison to “I’m just not the right person for you” or “I’m no good for you” or “You deserve so much better,” etc. But you’re not doing anyone any favors with self-deprecation. Sometimes the kindest thing you can do is to take ownership of your choices without trying to sell the other person on being okay with them. You’re not the right guy because you decided that you don’t want to be, and that’s a good enough reason!

“What do with sadness that I might never get married.”

Feel it, acknowledge it, sit with it, grieve about it for a while, and then channel whatever is left over into making a wonderful life for yourself. Write down all of your wildest dreams and do them as hard as you can, without waiting for someone else to make them possible. Married love is not the only kind of love. If you long to have children, married parents are not the only parents. Your life will happen to you whether or not anyone ever comes along to share it in the permanent, legal sense, so do you want to spend it waiting and wishing for what you don’t have or grabbing on with both hands?

My grandma Louise was one of four sisters. Two of them (Louise & Betty) were wartime brides, the other two (Rose and Aurora, who went by Aura) lost their sweethearts in the war and never met anyone they liked more. I don’t know what it was like to be young and unmarried and work their way through the 1950s and 60s as executive assistants surrounded by everybody’s Leave It To Beaver fantasies about what women should be, but when I came along in the 1970s, Rose and Aurora were retired and living together in a beautiful house on a giant piece of land in the middle of nowhere that they turned into a lush garden full of secret wading pools and fountains and long tree-lined paths. They had a riding lawnmower and giant floppy hats with veils to keep the sun off when they gardened and did yardwork. From the outside, their house was your basic mid-century split ranch, but inside it was like the lair of an elegant witch from a fairy tale. Their dining room furniture was upholstered in Barbie pink, and their house was full of books, closets with of elegant vintage dress-up clothes hanging in the backs, vases of cut flowers, lush houseplants, and souvenirs from their world travels like safaris in Africa and river cruises down the Amazon. The room I stayed in had a pink velvet-covered fainting couch in it, obviously the greatest piece of furniture ever built. They ate dessert every single night, sometimes before dinner, because Auntie Rose believed that life was short and that being a grownup meant doing whatever you want.

As a kid, I used to go stay with them for a few weeks every summer to get out of my parents’ hair and get space from my brothers, and their house seemed like a paradise. I wove fairy crowns of violets and read piles of books and tried on all of Auntie Rose’s bright lipstick shades and draped myself in silk shawls she brought back from India and learned to embroider cursive initials onto Auntie Aura’s tiny handkerchiefs and untangle her yarn for crocheting and generally did not one single thing that I did not enjoy or want to do for days on end.

Unlike at home, I was allowed to read at the dinner table because we all read books at the dinner table. Sometimes they’d have me read out loud to them, other times they’d read to me from whatever they happened to be reading. Auntie Aura liked Barbara Cartland romances and Auntie Rose liked non-fiction, especially history and geography, and whenever she got a new National Geographic she let me cut pictures out of the old ones and make collages and dioramas with them. There was no such thing as “children’s books” vs. “adult books” in that house, books were just books and I could read whatever I was able to understand. They’d give me chores, like dusting, which I did not mind because it gave me the opportunity to explore the house and touch all of their interesting stuff. They’d show me how to wash and dry their delicate teacups and saucers covered in gold trim and intricate floral patterns, how to correctly plump sofa cushions, and how to construct dinners entirely from shrimp cocktail, rare hamburgers, and fruit salads.

One of the only rules was that if was going to play their piano, I couldn’t noodle around on it, I had to play complete songs or nothing so if I wanted to play during my visit I’d need to prepare something and practice at home before I came. (I maintain this rule whenever I babysit my friend’s musically-inclined children, can’t recommend it enough.) On Sundays, they’d bribe me to go to church with them by letting me pick out their outfits and wear as much of their costume jewelry as I could pile onto myself, and then we’d all three go out for ice cream on the way home, filled with holy light and enough bling to blind everyone we encountered.

My memories of them are a child’s memories, obviously, so I don’t know what regrets or secrets they held. People can seem happy without being happy. They were both total babes, so I *highly* doubt that they did not have multiple options where romance was concerned, and it’s not like they were gonna tell a 10-year-old about any extramarital hijinx. And yet? I know they thought my Grandpa Oscar was irritating (accurate) and razzed him mercilessly, they often told me that men were “too much work,” and I do not get the sense that envied my Grandma’s life one bit. One time I asked Auntie Rose why she never got married after the war, and this is what she said: “I was so young and so in love, and once I stopped being young I never met anyone who could offer me anything that was better than what I already had.”

There are lots of ways to write a happy ending, and worse ones than “I lived with my best friend, doing exactly as we liked for 40+ years.” Your story will unfold, one way or another, so try to write the best one you can.

Hello Captain!

I think my friend (30F) resents my work-life balance? For a while now she’s been making these weird comments that I don’t know what to do with. I’m a freelancer (also 30F) with a lot of flexibility as to when I decide to get my work done and business is doing well! I’m happy. She works in corporate and is always complaining about being overworked. I wouldn’t mind that – I’m happy to emphathize but it’s often in passive aggressive ways?

I really try to not provoke her but it feels like I can’t say anything. The last time we called (it was a group call) I mentioned rearranging furniture in my room and she said: ‘Ha, you must be so bored’. Me: ‘No I wouldn’t say I was bored.’ Her: ‘Ive been wanting to clear out the fridge for a year but I have just so much work.’ Me: Silence

Also on that same phone call I said I was gonna make a coffee before meeting with my next client. It was a state holiday. My friend asked if I work today and I said yes. Then she goes: ‘Well at least you can take a break. I could never take a break during my normal work day’. Me: Aha. Moving on.

So it’s not like I’m shoving vacation pictures in her face. But she resents me mentioning I was shopping for groceries in the morning and stupid shit like that. I’ve stopped arranging meetups with people during normal work hours in the group chat she is because it really seemed to trigger her ‘well someone has to work!’ but I can’t keep from saying shit like ‘I’ve done a non work related thing’ or ‘I’m working’. She went to the same uni I did and could easily do the freelance job I do now – I’d be happy to help her out and offered previously. I don’t know what to say when she react like this and it’s getting on my nerves.

Lately I’ve been saying nothing and just letting the silence sit. Should I confront her about it? How? Or am I being to sensitive about it? It makes me want to not talk to her at all. I’m not sure she’s realising what she’s doing.

Hello! If I’m reading this right, it feels like your friend is negging you with these little comments, but you’re not sure if she’s doing it on purpose or if it’s worth calling her on it. You’ve been handling things just fine, sounds like, but now you have ample evidence that responding with silence does nothing to interrupt this dynamic and it’s still annoying you, so it’s time to try something else. Here are a few more active strategies you could try. All of them are designed to give you a way to test whether she’s doing it intentionally and interrupt the cycle, while also giving your friend the maximum good-faith opportunity to course-correct. Sound good?

Strategy One: Pattern recognition + Information diet

Your friend calls you, asks you what you’re up to, you tell her, and then it kicks off, right? Maybe…almost…. like she’s asking the question to give her an excuse to be weird and critical about it? Stop telling her what you’re up to, or use much less detail.

Her: “Hey, glad I caught you! And what are you up to this fine day?”

You: “Nice to hear your voice! What’s going on with you?”

Answer her question with a question. Or, even better, lie and say you are working, and see if that changes it.

Her: “Hey, is this a good time to talk?”

You: Sure! I just finishing up some work, but I’ve got a few minutes. Why, what’s up with you?”

I do not like lying as a rule, and I do not like people who make me feel like I have to lie, so I”m not suggesting this as a long-term approach. Think of it as an experiment, where for the next 10 calls from this friend where she asks you this question, working on work is work, so is housework, so is working out, so is working through your latest binge watch, so is working on catching up with sleep if she happened to catch you napping. Working on figuring out what’s for dinner? Technically work. Working on your golf swing? Through great effort great achievements are possible.

A person with no ulterior motives is going to roll with whatever you say you’re doing, and you’ll have a chill, normal conversation. A person who was hoping for a little fix of building herself up at your expense is going to get frustrated by this, and look for something else to latch onto. This is exactly what happened on that holiday when you had a meeting, right? “Well, at least you get some breaks.” Why not have a little fun with it and see how far she’ll go? If she gets bored and stops doing the annoying thing, you win.

Strategy Two: Meet passive-aggression with aggressive positivity.

Her sub-textual bullying can’t land if you ignore the subtext and engage only with the text of what she said. Is it true that you get more downtime in your workday than she does? Sounds like it. Do you feel insecure about how your schedule compares to hers? It sounds like you don’t, at all, so what happens if you treat her implied insults as if they are something between neutral, accurate observations and sincere compliments?

Her:“Must be nice to have so much free time.”

You: “You’re right, I love having such a flexible schedule!”

Her: “Wow, I could never just take a coffee break in the middle of the workday like that.”

You: “I agree, it is pretty great to be able to pace myself and set my own hours.” 

Her: “Well, *someone* has to work while you’re off [rearranging the furniture][making yourself the occasional beverage][running errands].”

You: “Hahaha, you’re so right! The best part is, if I bang out my work early enough in the day, I get to hit the grocery store in the afternoon when it’s not crowded and I don’t have to go on the weekends when it’s a madhouse in there.” “As you know, freelancing can be pretty all-or-nothing, so after a couple of busy weeks to hit deadlines, it’s really a relief to have some down time to catch up on the routine stuff.”

Be inexorable about turning every dig into sincere appreciation.

Why this works: If she doesn’t intend to be mean (doubtful, but let’s go with it for a second), then you’re just “yes-and”-ing her in a pleasant conversation. If she does intend to put you down, she’s gonna have to work much harder at it, meaning, she’ll either get bored and back off or your Ted Lasso-level positivity will annoy her so much she’ll change tactics to something more aggressive-aggressive where it’s crystal clear that she’s being mean to you on purpose and then you can deal with her on those terms.

Strategy Three: “Are you okay?”

This works best in person where you can see each other’s faces, and like the compliment strategy above, it works best when you wait for there to be an immediate example of the bad behavior rather than trying to discuss the overall dynamic in the abstract. Once she does the thing, pause, look her in the eyes, and maybe put a concerned, gentle hand on hers  and say, “Are you okay?”

Her: “What do you mean?”

You: “I asked if you’re okay.”

Her: “Yes, I heard you, but why?” (or “Of course I’m okay, why would you say that?”)

You: “I dunno, one second you were complaining about how hard you have it at work, which is valid, but then it felt like you were trying to put me down for having a different schedule. Was that your intention when you said [repeat back what she said, including her tone]? Something just feels ‘off’ so I’m asking, are you all right?”

Why this works:  If she’s doing this unconsciously, like it’s just a rote reaction to compare herself to other people to make herself feel better, then you’re calling it out in a direct and gentle way that gives her a chance to catch herself, apologize, and clarify her intentions. And, while I try to be a shoulder angel most of the time, allow me to put the shoulder-mounted devil costume back on for a minute: If she’s being mean on purpose, gently asking if she’s okay is actually a reverse-Uno condescension masterpiece that will drive her up the wall, but you’re not doing anything overtly mean to escalate the situation.

Remember, people have choices about how they treat you. She could say, “I’m so sorry, I didn’t mean to insult you, I’m just stressed out at work and frankly a little jealous of your ability to have more control over your time.” At which point you could say, “I understand if you need to vent about work sometimes, but can you do it without making little digs about my supposedly cushy life? Whether or not you mean it as a put-down, it feels like one and I’d like you to stop comparing our schedules from now on.”

Or, she could turn this into a bad-faith referendum about how she was “just joking” and the real problem is how you are just “too sensitive,” etc. For that, go back to the strategy of agreeing with negs until you can get the hell out of there. “You’re right, my schedule is better and I do have more free time. That is a problem….how?” “You’re right, I am sensitive when a friend can’t seem to talk about her own problems without making digs at me and my life.” “You’re right, I didn’t get the joke or find it funny! I guess we should probably stop talking about topics where we have such a different view of things.”

Strategy Four: “You’re being really weird about this.” “This is boring, let’s talk about something else!” Also known, broadly speaking, as returning awkwardness to sender.

There’s a very specific kind of bullying attempt that happens when an insecure, toxic person who is heavily invested in a cultural narrative that Following Certain Rules Will Make You Both Happy And Better Than Other People encounters an inexplicably (to them) happy person who stubbornly refuses to follow (or give a shit about) the same rules. I think you might be in a situation where this fits. .

Story Time [with content notes for fatphobic bullying and body stuff]: Long ago in the late nineteen hundreds I worked at a place where there were a ton of white women in our 20s who did roughly the same job. We became friendly, often ate lunch together, and went to happy hour and did fun stuff outside of work together occasionally on weekends. One of them I’ll call “Shelly” was obsessed with two things:

1. Being thin.
2. Getting a boyfriend.

For Shelly, these things were inextricably linked. Boyfriends were achievements that could be unlocked by becoming sufficiently thin, and both of these goals gave her an excuse to practice constant vigilance and constant comparisons to other women. You might wonder what she did when presented with incontrovertible proof that some fat women had boyfriends.They were obviously sluts! She sounds fun, right?

Shelly was not even close to my first ride on the Mean Girl Express, but I’m not a naturally confrontational person and I was actually mostly fine with tuning her crap out in group settings for the sake of hanging out with the coworkers I liked. Unfortunately, Shelly decided that I was meant to be her Sidekick/Fat Best Friend/Punching Bag and started singling me out, and the way she did it was *very* specific:

[A comment on whatever I was eating/wearing] + [A backhanded compliment about how she wished she could be that confident/careless] + [A reminder of how virtuous she was being by comparison] = Me wondering “What the hell just happened?”

“Oh my god, your sandwich looks so yummy! I wish I could have avocado on mine, but they have soooooooo much fat.”

“What a cute outfit! I didn’t know that [Retailer] had pants in bigger sizes now, back when I got mine I had to diet so hard to fit into them. I love your confidence!”

She loved to shop on her lunch breaks, and her favorite way to shop was to go to stores where nothing would fit me besides earrings and have me be an audience while she tried stuff on and she lamented about how fat everything made her look. It only took one of those for me to decide that being alone with her or going to a second location was not for me, so then she started bring bags of her “fat” clothes to the office to see if I wanted any of them before she donated them to charity, knowing full well that they would not fit me. Sometimes my shoulder angel wins, and I say stuff like “Oh, no thank you, but I appreciate the thought!” and sometimes shoulder devil is like “Oh, thanks for thinking of me, but our… tastes… are very different” while I rub the feel of the plastic garbage bag full of pilled acrylic sweaters the color of old mustard off my hands as if I’ve touched something gross and sticky. Don’t remember which shoulder bud was ascendant when, but eventually she did stop trying to foist her cast-offs on me or cajole to “Come on, just try them on!”

The thing with this kind of bully is that they *are* conforming to entrenched cultural narratives, so there is a lot of ambient background support for the idea that they are just striving in a normal way and anyone who doesn’t do the same is the problem. Mine was going all in on fatphobia, and yours is going with rise-and-grind capitalism, but the bargain they think they are making is the same. “I follow the Rules and do things Right, ergo I Deserve to be Happy and Successful!”

If other people manage to be happy and successful on their own terms, without putting themselves through the same hoops, these people find it between mystifying and threatening, depending on how miserable they are at any given moment. What good are the rules they’ve chosen to dedicate themselves to if the people who don’t follow them aren’t punished? You don’t have to openly antagonize them, you just have to exist where they can see you and that’s enough to constitute a personal attack on their way of life. In other words, if it’s possible for you to have a fulfilling career AND free time, then you exist as evidence that maybe the long hours your friend is putting herself through at work are not entirely necessary, and that’s scary for her, so she’s reminding herself of what she’s been taught about how all of this is supposed to work. If she were truly happy and secure with her choices, then she wouldn’t need to sell herself (and you, by proxy) so hard on the notion that her way is the best and only way. 

Like you said, if your friend feels overworked and is genuinely interested in how you pull it off, she could ask you for ideas about transitioning to something with a better schedule. If she were just venting about her situation, you could be a sympathetic ear. But the way she keeps making digs at your life shows that this isn’t about leaning on you for support.

I felt bad for Shelly, because her unhappiness was visible from space, but I flat out did not like her enough to hash any of this shit out. I was never going to convince her in a million years that the things she valued (male attention and having the smallest possible physical mass) were not worth the misery she was inflicting on herself and others. Would she have benefited from being professionally screened for eating disorders, or some other kind of therapy? Probably? Even if I had known such a thing existed, would she have listened to such a recommendation from The Fat Girl Who Embodied All Her Greatest Fears? Nope! I was not a Captain of Awkwardness yet but I did know that I was not causing her to behave like this and that trying to fix mean people is wasted effort. Any attempts to engage her on that level would have ended with her doubling down. But I did successfully get her to start avoiding me and stop talking about diets, etc. all the time by reacting authentically to how incredibly odd her behaviors were and how they made me feel without ever engaging with the substance of the comparisons.

“Wait, did you just mentally count the calories in my sandwich?” :nervous giggle: “Should we….like…go around in a circle so you can compare your lunch with everyone’s, or are we good with just mine?”

“Do you keep a spreadsheet of my clothing sizes somewhere? Can I see it?” :awkward pause: “Or do you do all the math in your head, that’s amazing!” :longer, more awkward pause:

“Oh, we just talked about diets and men yesterday, can today be for finding out about what books everyone’s reading lately? Or, we could talk about boys and books. This dude I went out with the other night brought me a copy of Confederacy of Dunces and said it was his favorite book ever and now I have questions.”

I’m riffing off of remembered vibes here, not recreating actual conversations word for word, and I definitely mixed it up with the turning negs-into-sincere-compliments thing without realizing it was a strategy. She’d give me one of her backhanded compliments, and inside my head, I would be like, wait, she said I was “so confident” but I think she meant it as an insult, but actually, I *am* pretty confident, so, yay for me! “Thanks, Shelly! You look nice, too! What’s everyone reading lately?” She HATED it, which is how I know she was being a bully on purpose. She mistook the fact that I don’t default to Mean Girl mode as a sign that I was incapable of matching her energy, and well, everybody learned some new things that year.

Why this worked: We were surrounded by fellow nice white ladies who were also on perpetual 1990s fat-free diets who did not really “do” open conflict, so they were no help whatsoever, but as long as I kept my tone pretty light there was nothing for them to latch onto except the subject-change-shaped-conversational-life-preservers. Over time, a few people who genuinely liked Shelly and wanted to talk about the same stuff closed ranks, and all the non-miserable folks were set free be lunch buddies with only some diet talk, some of the time.

To implement this with your friend, wait until a conversation where the pattern forms, and then keep your tone very, very relaxed and flat. “Huh, so strange that you keep comparing our schedules even though we do different jobs, what’s that about” (not really a question) and then change the subject. “Are you venting about your work schedule or criticizing mine? I lost track for a minute.” “I love it when you ask me what I’m up to and I think it’s going to be a fun conversation and then you immediately imply that I should be doing work.” “Did my ancestors send you to check up on my degenerate lifestyle again.” You’re not being mean or escalating conflict by calling attention to the conflict.

Strategy Five:  This person is your friend, and ultimately, directness is kindness. “It’s really strange that every time we talk about our schedules, you compare yours to mine in a way that feels insulting. What’s that about?” (actual question) “You keep doing this thing, do you realize? Well, now you know, so are you going to keep doing it?” “I really value our friendship, so I want to address this with you and figure out another way.”

Her answers will tell you everything you need to know about whether this is a friendship worth preserving. Life is too short for frenemies who manufacture excuses to be mean to you.

P.S. If you’ve seen the word “weird” in the news a lot want to talk about Returning Awkwardness To Sender as a political strategy, there’s a post over at Patreon all about that.

Dear Captain,

I (she/her) am thinking about moving in with my boyfriend (he/him) of 4 years. The problem is that I am afraid of losing my sense of self, and I don’t now if I can be, or want to be, 100% committed to him.

My boyfriend is wonderful in many ways. I love him, and really like spending time with him. I also tend to have better habits concerning sleep and food when I live with someone versus when I live on my own. So, co-habitation with him seems like a good choice. From former relationships, I know that I tend to care too much about my partner’s happiness, and forget to think about what I want. For example, I want to have more adventures than my boyfriend, but I might tell myself I am content with staying at home when he doesn’t want to join me. Maybe this is because as a woman in our patriarchal society, having a successful relationship with a man is seen as the objective.

I should also mention my long distance friend/former hookup, let’s call him Mr. Distance. We met five years ago and spent a couple of days together. We live on opposites ends of the continent, so we couldn’t date. We have have kept in touch, and met two more times as friends. Our conversation can still be a little bit flirty. It’s easy to fantasize and image a perfect relationship, when we never had one. In reality I think any relationship would crash and burn in less than than a year if we tried. But talking to him still gives me a thrill, that I miss in my daily life. It gives me a resort from the worries of everyday life, a space where I don’t have to care what anyone else thinks.

A work-friend of mine was diagnosed with cancer recently, and the first thing she did besides starting treatment was marrying her long time partner. That made me realize that if I had a year to live, I wouldn’t spend that year with my boyfriend. I would travel the world, alone or with Mr Distance. But if I am thinking about the long term future, then I don’t know what to do.

Kind regards,

Twined

Dear Twined,

There’s no rule that couples have to live together after a certain amount of time, and there are other ways to improve your sleep hygiene and eating habits than mixing your books with someone else’s books. If you’d rather not move in with your boyfriend, don’t.

If you decide to give living together a try despite your misgivings, put safeguards in place. For example, instead of combining your current rent payments to afford a bigger place, cut your housing payments in half by looking for a place that either of you could afford on your own if the other person moved out. Sock whatever you can into an emergency fund. Talk openly about how you both want money, housework, and house rules to work to make sure you’re on the same page, like you would with any potential roommate. Talk about what happens when the lease ends and make a plan to check in a few months before and decide for sure whether you want to renew (together, separately, at all) for another year. Lots of people move in with romantic partners as a compatibility test for eventual marriage or long-term cohabitation. Lots of those same people skip these conversations even when they explicitly call it a trial run, and I hear from them when they “can’t” break up without massively destabilizing their finances or access to safe housing.

“What do we do if one or both of us realizes that living together isn’t working?” is a scary question. Love yourselves and each other enough to ask the scary questions. Would your boyfriend want to move in with you in the first place if he knew about these doubts? Does he have doubts of his own, and is there something either of you could do that would make moving in easier to say yes or no to? Does delaying that step spell the end of your relationship, and is that risk worse than the alternative? ‘Cause I can tell you from experience that moving in with someone when you are unsure about the relationship and then realizing that you’ve made a huge mistake once you’re already locked in is in no way easier, cheaper, or better than breaking up or deciding to hold off until you’re truly ready. (Signed, a lady who looked at multiple studio apartments the same month she packed to move in with her ex)

You say “I want to have more adventures than my boyfriend, but I might tell myself I am content with staying at home when he doesn’t want to join me.” Is your boyfriend stopping you from having those adventures, or are you stopping you? Meaning, is this a “break up with people who make your world feel small” problem or is this a “please get a therapist and learn to do stuff without him” problem? “Mr. Distance” sounds like one of those motivating crushes, where it’s not so much about being with the person as it is liking the parts of yourself that come awake when you’re around him. The realization that you wouldn’t spend your last year on earth with your boyfriend is another version of the same message: There’s a happier version of you out there, and there is still time to become her! In your letter you are literally describing what it’s like to experience a call to adventure, so what would happen if you answered? If your life were a rom-com, you’d be in the part where the heroine has to date herself. 

Movie-Twined would have a pretty good relationship with a solid guy who wants her to move in with him, let’s call him Mr. Dependable, and she’d also have tempting Mr. Distance circling around. But”which guy does she pick” wouldn’t be the story, it would just be the rom-com shaped vessel for the real story about figuring out who she wants to be.

Fade in on Twined and Mr. Dependable as guests at a terminally ill coworker’s wedding, where the topic of “what would you do if you only had a year left” is on everyone’s mind. During wedding planning, the bride and groom made a giant list of all the places they want to go and everything they want to see and do over a lifetime together. They’ve written each adventure-task on a slip of paper, and put the slips into a giant bucket, and their plan at the wedding is to draw twelve slips, one for each month of the next year, and then distribute the leftovers between the guests. The couple will accomplish as many things as they can in the time they have, and then it’s up to the people they love to do the rest in their honor.

Twined ends up with three slips of paper. We don’t see what’s written on them before we head into a montage of tearful toasts, first dances, and other wedding reception staples while the soundtrack lays it on thick with At Last and Time In A Bottle and (I’ve Had) The Time Of My Life. By the time Ben Folds sticks the knife allllllllll the way in, we find a runny-mascara’d Twined out on the balcony for a little much-needed air. She’s finally looking at her “bucket list” items when Mr. Dependable comes up behind her and wraps his arms around her from behind, and the last thing we see is her, engulfed in his bear hug almost like she’s being strangled, the slips of paper clutched tightly in her hand. Each subsequent act of the movie will correspond to one of the slips as living out her friend’s dreams leads Twined to discover her own.

What are the adventures on the slips? You tell me. If I were really writing this as a movie, I might build a trio of the bride’s best friends, and each of them gets one adventure like it’s Sisterhood of the Traveling Pants-meets-Little Women-meets-Sitting In Bars With Cake. Since this is your story, you get to fill in the blanks with everything you’d rather be doing when you pretend to be content with staying home with your boyfriend. What could you do with a year?

You could get a therapist and ask them, “How do I figure out where I end and other people begin?”

You could devote one night a week to do something interesting outside of your house, invite your boyfriend or not invite him, and if he doesn’t want to join you, you could do it anyway.

You could finally learn to fence or play an instrument or do the moonwalk or get really into darkroom photography or roller derby or improv or a foreign language or whatever that thing is that you keep resolving to try every January 1 and then not doing.

You could close your eyes, spin a globe, and plan a trip to wherever your finger lands when it stops.

You could volunteer for a cause that you care about and do your bit to change the world.

You could make this the year you focus on making new friends and deepening ties you already have.

You could make this the year that you put in the work to level up in your chosen career field.

You could go to your nearest animal shelter and walk out with just one of the many loves of your life.

I don’t know, but you do. These are your sculptures, your potions, your traveling show, and this is your song. If the duet you’re currently singing has stopped feeling good, improvise something new.