User blogs

Dear Captain Awkward,

Last year we had a blow-up in the friend group involving a lot of brewing issues left unsaid (especially frustrating when I have made a point generally asking people to let me know if I am doing something that upsets them so that I can address it) and general communication problems. After a while of everyone feeling bad, we had a conversation to address it (which didn’t work for parts of it but that’s how it goes). In that conversation, it was brought up that I should have reached out to people, so afterwards I made a point of sending a message to each person to see if there’s anything they wanted to discuss with me one-on-one. Some did and we largely had good chats, or at least useful ones!

I messaged one friend who had specifically brought up a problem with me in the large group conversation to address said problem. They told me they were overwhelmed that day, but would get back to me the next day. After a couple weeks I messaged asking if they had sent me a message on another platform and I had missed it, or if they just hadn’t had the spoons to message yet. I specified that if it was the latter, that was totally find and understandable, I just wanted to check because my brain was getting anxious that *they* were waiting on *me* and getting frustrated about it. They told me that yes it was spoons (they’d had a death in the family, so that was very fair!) and they appreciated my patience.

It’s now been two and a half months since the initial message. I’m afraid to message again because of the fragile nature of everything after the initial blowup, and because it might seem demanding when the initial blowup placed myself and my partner largely in the wrong (that’s a whole other can of worms). My partner still talks to them casually on a semi-regular basis, and I’ve asked him not to pressure them on my behalf because that feels bad and would probably also go poorly anyway. I just don’t really know what to do at this point. I’ve been pulling away from the friend group more because being there makes me anxious about the one person who definitely does hate me after the blowup, and because the friend group is basically friend-who-won’t-get-back-to-me’s group (I would bet that they wouldn’t see it that way but many others would). I spent the first couple months anxious and spiraling about it most days, and now I’ve internally written them off as a friend to some extent… but that feels unfair and also still lacks closure. Maybe that’s how it has to be though.

Hello!

What the heck did you do to upset these people?  There’s a thread here of acknowledging that you were in the wrong but displacing some of that blame on how others failed to notify you in a timely manner or to discuss it at length to your satisfaction which is not emitting “reliable narrator” energy or (more importantly) helping you resolve this and feel better. It’s hard to fully answer without knowing what your part in the conflict is, but I can address your search for closure. Namely, closure is something you create for yourself, not something you demand from others.

So, what would you do if what you’ve been told so far is everything you’ll ever know?

Based on whatever discussions you’ve already had, what are the behaviors that need to change to avoid the same thing happening again in the future? Make a list. Is it a reasonable list? Like, you can see why these people are upset and acknowledge your role in upsetting them? Are there specific behaviors that could be addressed with effort, or is it more like “change your entire personality (but also we still won’t like you if you do)”?

If it’s a reasonable list, then change the behaviors to the best of your ability, without demanding more feedback or putting more emotional labor on others to correct you if you step out of line in the future. The time for “Let me know if I do something to piss you off” is over. You pissed them off. They let you know. The remainder of the “work” here is yours. Convert whatever issues they’ve made you aware of to date into self-awareness, and do your best not to repeat the same errors in the future. Sometimes that’s all you get, no credit, no applause, just the knowledge that you did your best to fix whatever is wrong and grow and learn from your mistakes. If it’s an unreasonable list of “actually we think you suck no matter what you do and you are now the group scapegoat for everything that’s wrong” then grieve the end of these relationships and do your best to move on. Sometimes the lesson is how there is no point in working on relationships with people who fundamentally do not like you.

Above all, assume that this one friend does not want to talk to you about this conflict anymore, perhaps ever. Stop chasing them! Someone died! They have made it clear that you are not their priority or focus at this time, which is not ambiguous! If they change their mind, they know where to find you. People mostly do not enjoy having fraught conversations about boundaries or constantly auditing the state of their relationships, and this person sound like they really don’t wanna do that with you.

If their lack of interest or ability to sit down and talk stuff out with you changes your own level of investment in the friendship, that is…. fine, actually? It doesn’t *feel* fine, but “withdrawing from relationships that don’t feel good to me” is something you can actually do about this that doesn’t make the problem worse. Channel your energy into relationships that aren’t a constant source of conflict and anxiety, ones where you feel safe and comfortable both giving and receiving feedback, and where you don’t have to tiptoe around people who hate your guts (which it sounds like at least one person does). Friend groups are not a monolith, so if a sincere apology and changed behavior on your part heals some of what’s broken with some of the people you like the most, hang out with them individually or in smaller-subgroups as long as it’s enjoyable for you. If finding compatible, comfortable, safe friendships means seeking some new friendships in this new year, then redirect your energy there and relegate these people to sometimes-friends you interact with occasionally via your partner. And if your anxiety is fucking with your ability to function and enjoy life, seek available anxiety treatments and see if that helps. At least consider that people who aren’t really speaking to you are unlikely to make you *less* anxious.

That is the best I can offer without knowing the nature of the initial rupture. For more about making amends even in the absence of participation of whoever you’re making amends to, I highly recommend On Repentance and Repair: Making Amends In An Unapologetic World by Danya Ruttenberg. It was one of my favorite reads of 2024.

Most Esteemed Captain Awkward:

My partner R (she/her) and I (she/her) have been together for 3+ years. She is definitely antsy to get engaged and I thought we’d be planning for children by now, but things have come up that make it hard for me to imagine taking the next step. We mostly have a great relationship, but R often has criticisms that boil down to me not being thoughtful enough. However, I genuinely don’t know how I can fix this. It’s tough because, due to my abusive childhood in a controlling religious (cult) environment, I have a lot of issues with Never Being Good Enough, and I get so triggered by R sometimes. I’m working hard on being less defensive in these situations, but I don’t know how to take accountability and apologize for something that I don’t actually think is wrong without sounding fake.

A few examples:

• A few months into dating, I learned a show I was obsessed with was leaving Broadway and decided to go see it before I couldn’t. I purchased two tickets and told R that I’d love for her to come but that I understood if she couldn’t. (I figured that if cost was an issue, she’d let me know and hopefully let me cover it, but I didn’t want to assume that would be OK or pressure her.) However, she was very offended and said I made her feel like I “wasn’t thinking of her at all.”

• R’s sister has a toddler and asked R’s mom to travel (~2 hr flight) to them to watch the kid while she went on vacation. R asked me if I wanted to join and I said no immediately. R was upset and said that I had “said no too quickly/I wasn’t thinking of her feelings/was thinking only of negatives.”

• I attended a conference that is directly related to my work but also personally important and meaningful to me (think, a teapot convention focusing on gay autistic tea pot makers) While we texted constantly and talked daily, R was anxious and accusatory, asking me if I was distracted or if I’d been drinking. On the first full day of conference activities, R sent me a text making it clear she felt “not like a priority” and was upset with me. I immediately called her, but she would not talk because she said I sounded upset. (Fair! I was!) We talked it out over several hours the next morning, with me missing most of the conference events I’d been looking forward to.

• Recently, it was her birthday. After weeks of asking what she’d like, she told me she just wanted a specific cake, which I promptly ordered. I did some fun decor (balloons, streamers, etc) at our house, too. The weekend seemed OK but on Monday (her actual birthday) she sent me a text saying she didn’t want to have her birthday dinner because I had failed to wish her a happy birthday and bring her coffee in bed. When she got home, we had a really horrible fight where she detailed the ways I have failed re: her birthday- it was detailed: not putting cupcakes on a plate or doing candles correctly, while attributing these failures to (apparently) my fear of vulnerability and inability to follow through. 

I am trying to be less defensive when R brings up ways I’ve hurt her, but I fear that R has expectations that I cannot meet. Sometimes it almost feels like, in R’s mind, a negative emotion = evidence that I’ve done something wrong. With the first conflict about the trip, I can understand feeling a little taken aback and hurt that I was prepared to make the trip solo if she said no, but I disagree that this means I did something wrong. With the child care situation, I get being disappointed that I said no, but I disagree that it’s reasonable to criticize me for saying no too fast. Am I just too set in my ways? Can I help her to understand how this is affecting me? Is this even fixable? Am I a thoughtless ADHD jerk?

Happy Holidays,

Never Getting it Right

Happy 2025 and other holidays yourself!

Don’t marry someone who shits on your enthusiasm or regularly reminds you of what it was like to grow up in an abusive cult, is my advice for fellow ADHD-ers and everyone.

You describe a pattern where your partner continually ruins nice things you do for her and fun things you do for you. You also describe a pattern where you communicate straightforwardly, she does not, and then she punishes you for not having read her mind. Worse yet, instead of arguing about the specifics what you did vs. what she expected with an eye to better defining expectations or finding solutions for the future, the fights devolve into arguments about what kind of person you are (thoughtless). That is a sure sign of bad faith, right up there with “the more effort you make to understand the other person’s point of view and communicate yours, the worse it gets.” And I think you nailed it when you noticed that her negative emotions get recycled into excuses to blame you, which is an extremely common incubator for emotional abuse.

People have choices about how they treat you, so let’s review her choices relative to her available options at the time.

She made you feel bad about an objectively awesome thing, like getting tickets to your favorite Broadway show and inviting your shiny new girlfriend along. If she had had logistical or financial concerns that prevented her from saying yes, what stopped her from raising them? Her: “I’d love to but money is tight just now.”‘ You: “I totally understand. My treat!” Her: “Oh no, I’d love to, but that doesn’t work with my schedule.”/”I’m not really into that show.” You: “I totally understand, I had to jump on the tickets to get seats at all. But no pressure! I’ll find an friend to go with and we’ll plan something together another time.”

She couldn’t stop you from going on the work trip outright, so instead she manipulated you into spending most of it on the phone, reassuring her that she was a priority and dodging accusations that you were drinking. So what if you *were* drinking? You’re an adult, was that not allowed for some reason? And so what if your priority during that trip was to do work and make the professional connections you came to make? What would keeping you on the phone for hours get her that the words “Have fun, let’s talk when you get back” wouldn’t solve, besides controlling your time and attention and making you feel guilty? Why is you getting to do a job you care about with people who get you a bad thing? A partner is not a pacifier!

She’s had three birthdays and counting to answer the question “What do you want to do for your birthday?” with “I’d love my favorite cake on the fanciest plate we have, but my dream is to be awakened with birthday coffee in bed.” If you’d known how important it was to her, you would have done it in a heartbeat. And yet, she is mad at you for not doing stuff she never told you about, even when you asked her direct questions about what she wanted. She’s also completely unappreciative of the nice stuff you did do. The fact that she punished herself by canceling her birthday dinner just so she could make you feel extra bad about it is certainly a choice, but it’s not something you caused by existing within a non-standard brain.

I’ll confess, the “You said ‘no’ to babysitting too fast” example made me cackle with self-recognition. If she wanted you to come along, she has a right to be sad that you declined, she’s ultimately claiming to be mad that you didn’t fake interest in going before you declined. She could have communicated her disappointment, asked if there was anything that would make you reconsider, or laughed and said “Wow, tell me how you really feel!” But she couldn’t resist an opportunity for critique.

In my experience, when someone harps that you didn’t ask a question or say no just right, it’s usually because they don’t think you should have been allowed to ask that question or say no at all, but they have juuuuuuuust enough self awareness to know that if they admit that, they’ll definitely lose the argument.

This lady seems like she is very bad at being your partner.  Life is hard enough without turning fun, optional things into arguments! If she wants someone who will never buy tickets to fun shit on the spur of a moment or blurt out an answer, then she clearly wants a different person! She has the option to stop tormenting you anytime and find someone who communicates telepathically.

And yet, your email subject line was “Am I A Big, Thoughtless, ADHD Jerk?” and your question contains a troubling pattern that I’ve observed in multiple letters from neurodivergent people, people with diagnosed mental health conditions, and people with past or ongoing experiences of abuse (and associated Venn diagrams):

a) The assumption that a history of trauma and/or a complicated brain makes you an unreliable narrator of your own life who cannot *ever* trust your feelings or reactions.

b) Leading to the assumption that you are automatically the weakest link in any unrewarding relationship or intractable interpersonal conflict.

c) Followed by the assumption that the best way to repair situations that hurt you is by repairing yourself. You will always be an imperfect being, and there will always be more You to work on, so the fact that self-improvement doesn’t work the first or tenth or one hundredth time doesn’t mean the cycle can’t repeat indefinitely!

I will never argue that trauma, mental illness, and neurodivergence have *no* effect on one’s daily experience or relationships, and if they are interfering with yours it’s worth seeking available treatment. But I will argue that when you are engaging with someone who is unkind to you, “How can I fix myself to be more ‘normal’ and make my reactions to their bad behavior smaller and more palatable?” is not only NOT the solution to the problem, it’s a dangerous trap. There is no amount of “work” you can do — no therapy, no medication, no accommodations or workarounds, no amount of masking or policing your emotions that will magically make someone stop being mean to you once they’ve started. Pretending otherwise only ever serves people who want to continue to abuse and exploit you without consequences (and their enablers).

The longer you focus on your reactions to an abusive person’s behavior, question your own judgment, and sink more and more effort into fixing and sustaining the relationship, the longer you linger in harm’s way, and the longer you reinforce the lie that if other people are assholes to you, it’s most likely because something inside you made them treat you like that.

Let’s talk about how your childhood history is rippling through this situation. Often when people invoke trauma triggers, they talking about problems like a) flashbacks and outsized reactions to present stimuli inspired by reminders of the past or encountering similar circumstances in the present and b) behaviors that helped them survive in a stressful environment that don’t translate well to *dissimilar* contexts.

If a zero-abuse world is impossible, it would be super cool if everyone only ever encountered *one* abusive situation or person in life, and that once you got through yours, you get to mark yourself safe and be done for good. But life doesn’t work like that. For abuse survivors, the necessary skill isn’t automatically banishing every troublingly familiar warning bell or negative feeling to the emotional spam filter while you take more deep breaths or count yellow things nearby or remind yourself that it’s probably all in your head. Skills for self-soothing and grounding oneself in present circumstances can be quite useful! But so are discernment and pattern recognition: Asking: “Am I reacting to something that is happening here, and now, in this room or am I reacting based on past experience or manufactured future fear?” only works if everyone understands that one possible answer is “YES, RUN AWAY, NOW!”

In other words, if your partner’s brand of making you feel like you’ll never be good enough (so that you’ll blame yourself and try harder to anticipate her needs) reminds you of how you felt growing up inside an abusive cult, the simplest answer is that it feels familiar because it is familiar. That defensiveness, anger, and sense of unreality you feel about the situations you described aren’t overreactions or artifacts of past abuse, they’re understandable reactions to how you’re being treated in the present. And your reluctance to tie the knot and your timely request for help aren’t a sign that your brain works “wrong.” These are your self-preservation instincts trying to protect you from committing to someone who makes you unhappy. Can you imagine trying to plan an entire wedding with someone who can’t answer basic questions about what she wants honestly, thinks everything you do is wrong, and everything that goes wrong is somehow your fault? NO!

You asked: Is any of this fixable?

Not from inside the relationship and not on any kind of predictable timeline. Once you break up, a lot of stuff will get instantly fixed for you, in that you won’t be around a person who continually steals your joy and erodes your sense of self. You’ll be able to lick your wounds and find a compatible, nice person who is enthusiastic about you when you’re ready.

For your partner to fix anything, she’d have to own the problem, go to a therapist, ask, “Why do I belittle, blame, and try to control my partner whenever I feel bad?” and do whatever years of work are involved in unpacking that question and choosing a different way to be. Somebody who can turn theater tickets and birthday cake into an excuse to be mean to you does not seem likely to do *any* of that anytime soon, and I think attempting to talk to her into it is only going to buy you more bullshit.

Be swift, be quiet, and go. Then pick up your loud, beautiful life where you left off before this person crawled up inside it. Love and solidarity, always.

Ahoy Cap!

You have taught me a lot. I love how you parse situations. I thought of you while this was happening but am not sure I played it right…what do you think? Edit if you need, I know it’s long.

I am a chronically single geeky cishet woman in my 30s coming out of a several years’ bout of depression and anxiety. A few months ago, I got up the guts to turn on my dating profile. I am always stressed when dating, as I constantly worry I’m doing it wrong and in my awkwardness and low self-esteem will get myself into a situation I’m actually not happy in. It’s hard to envision myself in a relationship; I don’t know what I’d be like in one. But I figured I could not conquer this unknown without trying. 

Happily, I quickly began chatting with a clever, funny, geeky guy a few years older than me. We met for a first date, and I actually had butterflies! We chatted for three hours easily. I was nervous, but excited. 

Second date a week later, he wanted to meet me at his place and then go out for dinner. This made me a little uncomfortable, as for safety reasons I don’t want to be alone with someone in their home until I know them well, but I felt it would be impolite to wait outside his door and instead hurried us to dinner. The conversation was different this time. I felt like every third minute he was giving me ridiculously exaggerated but heartfelt compliments, to the point I became uncomfortable. I finally said something like, “If I’m the most interesting person you’ve met in years, you need to meet more people!” But he laughed it off and kept going. After dinner, he wanted to go back to his place and watch a movie. Now, important note: I want to save sex for marriage, this was clear on my profile, and he claimed he did too. What he wanted to do at his apartment was kiss me (that was welcome,) cuddle (I squirmed away and said I wasn’t comfortable with that,) and then give me a foot massage (I definitely wasn’t comfortable with that, especially since he asked by just grabbing my foot.) I was disoriented and discovered around that time that I needed to leave. 

By the time I got home, I had my head on straight again, so I texted him that while I appreciated the gesture, cuddling and foot massages were too intimate for me to feel comfortable with at this point. I paid close attention to his response: without a trace of pouting or guilting me, he apologized and asked what I was and wasn’t comfortable with. Since he had responded well, I decided to give him another date.

Third date a week later lasted a full day, again full of compliments and vague, maybe-not-literal (?) hints that he would like to buy me expensive presents or take me on trips. But nothing at his place and no attempted nonconsensual massages. I was trying to walk the line of being kind and appreciative of the very real effort he was putting forth without enticing anything further, as I felt he was moving very fast. He told a story about how he was making so much effort because he thought that’s what a woman deserved and to tell him if it was too much. I agreed that it was on me to tell him if it was too much. We did both agree that we had no desire to see other people going forward.

A week later, I requested we just get breakfast instead of spending the full day together, as I was becoming very exhausted and drained from all this and needed a weekend off. He was disappointed but agreed. At breakfast, he again started with the compliments, requested again that I tell him if this was all too much, and then said he really wanted to treat me right and not scare me off because he knew what he wanted, I was it, he loved me.

As soon as he said “love,” the first thought that went through my mind was: “shit, there goes that.” After breakfast, I stalked angrily through the grocery store having imaginary arguments with him about how he didn’t know me near well enough to know if he loved me. I called him later that day to break up with him. I told him that I was concerned not that he had strong emotions, but that he was not questioning these emotions and instead was rushing to judgement and action instead of reflecting critically. 

He was miserable. He did not try to guilt me but expressed that he wished he hadn’t told me he loved me. He expressed doubt that it was such a big deal to say “love”, as “love” to him just means “like a lot”. He asked if I could keep seeing him knowing that he just meant to communicate that he “liked me a lot”.

I said no. This man was older than me, claimed to be experienced with relationships, and had lived in the U.S. (where I am) for 30 years. I don’t know how he could get the idea saying “I love you” just means “I like you a lot” to your average American; it seemed either a last-ditch deception or a strong indication that his social skills were even worse than mine. I said I couldn’t imagine how we could move forward while both keeping our heads now that I knew he had such strong feelings. I would feel pressured to move faster than I wanted, and he would feel resentful of my delay. He promised he would go at any pace I wanted and would not in fact resent it, but I said I couldn’t risk it. He ended by saying that I didn’t have much relationship experience, and one day perhaps I will change my mind. If so, he would be ready. 

In the months since then, he has occasionally sent little notes and texts – not any discussion of what happened, but funny, flirty things like he sent before. I haven’t responded.

I felt gutted but decided about my choice to end this until one friend I told did a very bad job disguising her disagreement. While she was trying to be supportive, her questions clearly signaled she thought I was self-sabotaging by breaking up with a man for…liking me. She questioned whether the early L-word use might be cultural (his family immigrated here) or else a honest mistake by a socially awkward, fallible human. She seems to think I have massively overreacted out of my anxiety around relationships. It was enough to kick off my self-doubt vicious cycle. It now grates on me for hours every time he texts. Each time I remind myself I shouldn’t text back, I feel like I’m sucker-punching the sweet small town guy in the Hallmark movie that only wants to be good to the bitchy, cold-hearted big city lady.

What do you think? Did I gut punch Brayden? Or, alternatively, do you have any ideas of how I could have played this better so I can learn from the experience?

-Not a Lawyer, but that would be cool

Dear Not A Lawyer:

Your “readiness” for *a* relationship is not the issue with why this particular relationship didn’t blossom, and it’s not something you need to “work” on. Realizing that you are not on the same page with someone during the early stages of dating is not a failure. It’s what the early stages of dating are for!

Let’s review: You had a pretty good first date which did its job, which was to give you enough information to know whether you’d like a second date. The second date was incredibly Not Good. You felt cornered and coerced. After you squirmed away from him all night and told him you how uncomfortable he’d made you, he decided that for your third date, nothing remained for him but to assure you in the most animated language of the violence of his affection. When “I love you” did not have the desired results, he tried to both walk it back and blame your “lack of experience” for your rejection of his “love,” while also promising to wait for you.  Yikes on trikes on pikes near dykes! And your friend not only fell for this blatant ‘negging’ but tried to double down? No likes!

If you go on three dates with someone and each date is successively less enjoyable, that’s a great reason to not go on any more dates. If someone declares that they’re in love with you, and your gut instincts say “ohhhhhhh noooooooo,” that’s not a sign that you need to work on yourself until your feelings rhyme with theirs. It’s a sign that you need to stop trying to talk yourself into developing feelings for someone whose texts make you flinch and feel annoyed for days at a time. You gave guy multiple chances, and everything you described about his attempts to escalate intimacy well beyond your stated desires and boundaries made me flinch for you. ( I actually yelled “NO!” when he pounced on your unsuspecting foot.) “I flinch from your touch….and also your words…and also whenever I’m reminded that you exist” is an incredibly good reason to not date someone or be friends with them. The only script or explanation you need is, “Sorry, I’m just not feeling it.”

Good job tuning out your friend’s shitty advice and her excuses for this guy’s cloying behavior! If he’s so great, she can date him (I don’t advise it, but she certainly can.) Good job spotting red flags, sticking to your boundaries, and recognizing that this guy is “in love with you” the way Pepé le Peu is “in love” with the poor cat he’s mistaken for a skunk. He wants to be in love so bad that the closest being that sort of fits his template will do, and he’s trotting out his strategems* for “how to treat women” instead of listening to you about how to treat you. 

*Exhaust them, mostly.

This skunk has chased you long enough, I think, and you owe him nothing. I recommend that you block his number, block him on all the apps, and see if you can preemptively block him from being able to follow or see any social media accounts you have. Do not attempt to notify, explain, or apologize, and do not reply to *anything* he says or does to get around the blocks. Blocking someone after they declare their love, get dumped, and keep right on texting despite receiving no response is not an unclear or mysterious move. It means: “I don’t want this. Stop.”

If you are indeed worried that a lack of dating experience is holding you back in some ways, it has never been easier to go on more low-stakes first dates with more nice people and see if something clicks. Meeting more people will give you more information about what you like. It sounds like what you like is someone who treats you like a friend with the possibility of romance, and you don’t like surprise feet stuff or people who come on strong with boilerplate romantic declarations. (Hard same, honestly!) We are all flawed beings, but please get out of the mindset that your flaws mean you have to put up with stuff that gives you the ick. Feelings aren’t fair, and everything about your story is a reason to be more discerning (“picky”) about who you spend time with, not less. So continue to move at your own pace, and pay attention to reciprocity, safety, and your own enjoyment, and trust that the right people for you will not make you feel like you’re being chased. And remember, someone can be very nice, very into you, and do everything technically right, and still not be your person.

Thank you for your letter. Please allow me to build a general 2025 precept, akin to “Do Less Work” upon it:

Feelings are information. Stop talking yourself into or out of your feelings. Especially stop beating yourself up for not feeling what you think you should feel, and start listening to what your actual feelings are trying to tell you. Not every feeling is helpful or needs to be acted upon, but good news, you can decide what you want to do about your feelings later, as its own separate step! Just, it’s very hard to both make good decisions about a feeling and talk yourself out of having that feeling at the same time.

It is time for the periodic ritual where we treat the search strings people typed in like actual questions. All snap judgments, no context, let’s do it!

1) “Friend always forgets credit card.”

Forgetting a payment method once in a great while is a regrettable error. Forgetting it “always” (and not following up immediately to pay some other way or following through on treating next time) indicates a game of Awkward Chicken is afoot, where they are basically daring you to speak up and calculating that you’ll find it less awkward to pay.

Take the dare!

Stop making plans that cost money with this person until you’ve addressed the problem, and ask for separate checks up front whenever possible to minimize room for shenanigans. When you do address it, instead of hinting around or accusing them of forgetting on purpose (and getting blasted with shame and defensiveness), be blunt and direct about what you want to happen now/next. “Your half is $X, can you Venmo me right now?” “You still owe me $Y from last time, so I’d rather not do anything that costs money until we’re square. Can you pay me back today or should we plan something free?”

2) “Brand new boyfriend asked to borrow money.”

Nope!

I’m in no position to judge people for the fact of struggling financially, but in my experience, asking a brand new partner to lend money beyond “Can you snag us advance movie tickets and I’ll grab the dinner?” is among the most crimson of flags. It ranks only slightly behind a) “suddenly” losing their housing situation and needing to move in right after the first “I love yous” are exchanged (#hobosexuality), b) having a ton of bullshit reasons about why they “can’t” or “don’t have to” wear condoms, and c) any sentences that include the words “If you really loved me, you would_____.,” “It’s okay, my wife is cool with it,”  or “You’re not like other girls.”

Consider the possibilities, none of them great:

• They are disingenuous or unrealistic about their financial situation. And if the loan is for an investment “opportunity” or to bail out a flailing “business”? RUN AWAY.
• Even if everything is mostly on the up-and-up, lending money adds stress and tension to a brand new relationship. What is the plan and timeline for paying you back? Are you going to have to chase them down for the money or play Awkward Chicken? They are, at minimum, willing to put the relationship at risk over money, which does not point to them having great boundaries.
• Consider that they have no one else to ask because everyone they already know is tapped out or reasonably skeptical of their ability to pay it back. Just because someone doesn’t have a [therapist][single friend or family member in the world][rescuer/meal ticket] doesn’t make you the default substitute!
• It’s a test of whether you have porous boundaries and are prone to manipulation.

Fortunately there is a magic word that will both protect you and reveal bad intentions instantly: Say no and see what happens. Does the person try to manipulate you further? Or blame you for their issues? “I can’t believe you’d make such a big deal over something like money.” Saying that you’re not comfortable lending money to someone you basically just met is not mean or unfair. What would this person do if they didn’t have you to lean on? Sounds like they should make that Plan A!

I don’t know how far apart these next searches took place but I’m sensing a theme here.

3) “How can I get an old friend to stop calling me after 24 years?” 

You can’t get people to stop doing anything. You can either ask them outright to stop calling and see what they do, or you can adjust how–and whether–you answer. After 24 years, hearing some version of  “I appreciate all the effort you make to stay in touch, and I wish you well, but I think this friendship has run its course for me and I’d rather not stay in touch by phone anymore” will doubtless hurt. Will it hurt less than being ghosted, or whatever has you dodging this person’s calls?

4) “Old friend appeared out of nowhere and is overeager,”

4) Mismatches in friendly enthusiasm and reciprocity are inherently awkward, even if everyone is basically nice and has the best of intentions. Whenever someone clearly wants more from you than you want to give, my go-to advice is to figure out what level of interaction –if any!–would make you most happy and comfortable, and default to that.instead of trying to strategize around the feelings and expectations of a person you’re  already not terribly invested in.

If you’d rather not resume the friendship at all, then it’s probably better to just end it swiftly (see above).  If you’re open to seeing if a sometimes-friendship is possible, honor your own preferences about frequency and intensity of communication and see what happens. For example, they want to hang out in person every week, and you’d be happy to catch up once every three months? Then invite* them to hang out roughly every three months and politely decline everything in the interim. They want to text or talk on the phone all the time? “Sorry, I’m not much of a texter, please don’t be offended if I don’t reply right away. But maybe we can get together for lunch next month and catch up. How’s [date] or [date] for you?” If the periodic interactions are fun and planning them is easy, you might end up building a new friendship on the ashes of the old. Or, they might not want a “sometimes” friend, in which case, they are free to back away at any time.

*Note: If you take the initiative to invite them, then you potentially forestall a situation where they feel like they need to chase you. If you can’t see yourself inviting them to do stuff ever, remember: You’re not required to be friends with everyone who wants to be friends with you.

5) “Should I ask an old friend who doesn’t contact me out for a drink on her birthday?”

“Should” is a strong word, depending on the history, but you certainly can! If you’ve fallen out of touch, I’d assume your friend probably has other plans on her birthday, but it’s as good an excuse as any to reach out. “Hey, saw your birthday was coming up and realized I hadn’t seen your face in forever. Can I take you out for a drink sometime next week? Maybe on [date] or [date]*? Let me know, I’d love to catch up. Happy birthday in any case!”

She’ll either say yes or no, and then you’ll have your answer about whether “doesn’t” means “prefers not to.”

*Note: I’m putting language about nailing down a specific day for plans in these sample scripts on purpose. “Would you like to have a drink sometime?” is not making a plan, it’s assigning the other person homework to come up with a plan. It also allows people to say “yes” in theory and never actually make the plan, leaving you wondering if you’d be bothering them if you follow up with a plan. If you’re anxious about the situation at all, ambiguity just creates more anxiety. If you want to hang out with a given person, invite them to something concrete that they can say yes or no to.

6) “Boyfriend’s family won’t respect me until he proposes.”

Bad news: People who create arbitrary milestones after which they *might* theoretically respect you are pretending that you can audition for or earn their respect, like, “Clean the house, Cinderella, and then maybe you can go to the ball!” They want you to think that their disrespect is your fault and that you just need to wait longer or work harder to earn their respect. But there will always be another milestone or more work you’re supposed to do.

People either treat you with respect or they don’t. If these people don’t, and most likely never will, how bad do you still want to marry this guy?

7) “Mom has helped me financially now wants bank password.”

There’s a fine line between “help” and “control.”

Financial gifts and temporary loans with generous and unambiguous repayment terms are helpful.

Setting some boundaries and conditions around financial help for an adult child isn’t unreasonable. “You can live at home for free as long as you’re in school or studying toward a trade.” “This is the third time you’ve needed ’emergency’ money in as many months. I’m not sending more until we can sit down together and work out a budget so that this won’t keep happening.” (Providing financially for a minor child isn’t “help,” it’s non-optional support, so I’m assuming everyone in this question is an adult.)

But unless there are *incredibly* mitigating circumstances (like, you are incapacitated in some way), allowing a parent 24-7 access to both your money and your transaction history risks crossing the line into control. If your mom wants to be repaid for her help, work out a schedule and stick to it, but hold onto your passwords. And if control is the price of your mom’s help, think carefully about whether the cost is worth it. Sometimes the cheapest way to pay is with money.

8) “Parents freak out over not knowing my friends. I’m 24!”

I wonder, are your friends local or do they live inside the internet? Some of my best friends live there, it’s not weird like it was back in the 1990s when I just told my folks that everybody I knew from the internet was “a friend from college” or “former coworker” so they wouldn’t obsess about me ending up on Dateline.

If at least some of your friends are local and up for a challenge, I propose the following solution: Throw a little dinner party where you invite one or two of your of most outgoing friends and your parents. Cook something simple. Keep the music low enough to talk over without yelling and skip the recreational intoxicants. If your parents attempt to grill your friends about their education, hobbies, love lives, and career prospects, see if you and your friends can band together and take turns asking them the same questions. “What do you do? How’d you get into that field? Do you like it?” “When you were our age, what did you do for fun?” “What was dating like in the Olden Times?” “Have YOU read any good books lately?” Maybe play a wholesome party game like Time’s Up or Apples to Apples. Neutral-boring is better than bad-interesting, so when in doubt, be boring.

This won’t magically undo the worry about loss of control, passage of time, sense of competition for your time and attention, or whatever underlying fear that’s causing your parents to “freak out.” But this has the advantage of addressing the thing they say they are worried about head-on: “You didn’t know my friends, but now you do! We just spent two pleasant hours being adults together!” Removing the mystery might inspire your parents to seek something new to complain about.

If your friends live mostly online, or you can’t yeet your friendly neighborhood Commander Logic at them the way every single person in our friend group does (she is truly THE BEST at Parents), you might get mileage out of asking your parents to be more specific about their worry and see if explaining it aloud either makes it progressively less worrying over time or gives you a more specific way to address it. “So you’re worried about me driving at night? Would it make you feel better if I texted you when I got there?” If they keep adding worry on top of worry the more you try to meet them halfway, at least you can be sure it’s not something you’re doing and stop giving them more ammunition. Ultimately, it’s pretty normal to have a social life that’s separate from your parents, so don’t let their worry stop you from enjoying your life.

9) “Every time I try to rest or sleep my mum calls me why is this.”

THEY SEE YOU WHEN YOU’RE SLEEPING

THEY KNOW WHEN YOU’RE AWAKE

No, wait, that’s Santa. I don’t know why your mom does this, but I do know that most phones nowadays have many “do not disturb” settings that will silence notifications or filter them from specific numbers. USE THEM. And if she still somehow gets through, don’t answer until you’re ready to be up and interactive.

If these are calls coming from inside the house, I don’t have much helpful advice. Having encountered several people who assume that “my rest time” = “their time that could be put to more productive use,” I tend to get as far away as I can and stay there for as long as I can. Hard when it’s your mum and you live in the same house, but hopefully not impossible forever.

10) “babby MUST calm DOWN”

Most of what I know about how is babby comes from memes, but I will try:

First, why babby is excite? Hold babby? Feed babby? Change babby diaper?

If not hungry-lonely-wet, maybe put babby in car seat. Then drive. Babby sleep?

That’s all she wrote, for now. Wishing you all the best of the rest of this winter holiday season, and thanks for reading!

Dear Captain,

My partner (40s, he/him) and I (30s she/her) are both artists. I come from a rich family and he comes from a poor family. Unfortunately where we come from, the starving artist cliché is completely true. Even though my partner is very talented and has done well for himself, his financial life strategy consists of sometimes amassing money (from sales of work or from grants) and then living frugally and slowly whittling it down until it completely runs out.

This can be very, very stressful. I feel guilty about even putting this into words because I live off my inheritance, and gave up having a different, non-creative, but more lucrative, career, because I knew I could afford it. We live in an apartment I own outright. He pays bills and I pay the admin fees (I pay about twice what he pays). I sometimes find myself becoming overwhelmed with resentment at him because I feel like he can’t support any long-term financial plans I have for myself or for our life together, and I know that in any emergency I’m going to have to foot the bill.

During our six years together he’s had to live with multiple roommates to afford rent, he’s been unable to afford health insurance or therapy at times, and everything is mediated by the looming threat of his money running out. He also has several aging relatives with declining health that don’t have a pension. He insists that he’s always worked it out, he’s never gone into debt and ultimately none of this should affect me. It is true that he’s never asked me for money, and he’s contributed to our household in many other ways. He’s wonderful and loving, and he’s my best friend in the world.

I could probably afford to support him financially for the rest of both of our lives, but I’m not sure I want to. We’ve already broken up over this once, and are in a shaky place at the moment. I’m not sure how to handle the situation, and he feels very insecure and defensive whenever I try to bring up the stress I feel about the money situation. I feel like we’re at a stage of the relationship where I wish I could see myself getting married and building a whole life with this person, but this keeps holding me back. What should I do?