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Ahoy Captain! I

(31 she/her) am currently dating “J” (32 he/him). We’ve been dating for a little over a year now. Things are going well, except for one thing…he isn’t divorced, and I’m not sure that he wants to be. Any scripts for a conversation around that topic are greatly needed.When we began dating last year in 2022, he told me he was in the process of a divorce, and that he and his former spouse had parted ways in 2020. He told me that the former spouse ended things, and moved out in 2020. They never had any children,or owned any pets together. Their home was an apartment that they rented, so when they stopped living together, they did not have a home to sell, and the landlord rented that apartment to someone else.

I was of the understanding that the divorce would be finalized by the end of 2022…until J let me know that they still needed to file for divorce. Which threw me for a loop. I bring up that they never had kids/pets/property together, because from what I can tell, in the absence of this, shouldn’t the divorce be pretty simple? But maybe I was wrong. I’m no lawyer. So I accepted that maybe some hiccups had happened–it’s not like the legal system is that great anyhow.And then he let me know back in July they still hadn’t filed for divorce yet–but was supposedly working on it–and alarm bells went off in my head. I don’t know how to have a conversation about divorce.

I was single for a long time before meeting J, and he’s my first Serious Relationship. I’m so sad I’ve been with someone who, aside from this issue, is a great person. He makes me smile, I feel safe with him, he takes the time to call me and check on me, etc. I can say with total sincerity he is one of the most caring people I know.He was with former spouse for nine years. His home life was pretty chaotic, and he got married young partly to escape that. I don’t know what it’s like to have been with someone for nearly a decade, to grow from your teens to your late twenties with them, and then to have to figure out who you are apart from that relationship. I was sorry to hear that two of them grew apart as people, but not surprised. People often have more growing to do in their mid to late twenties, and I’ve been several marriages collapse between people who both were married before age 25.

We spend every weekend together, call each other at least weekly, have met each other’s families, traveled together, etc. My parents have asked about marriage, and I’m of the understanding his family has wondered the same. We’ve talked about trying to have kids together, and are on the same page. I could see this relationship lasting years, and I don’t feel comfortable having kids with someone outside of marriage, not because of moral ones, but because of legal logistics, such as being on the same health insurance, paid parental leave, who gets what last name, etc. How do I even approach this conversation with him? I want to be sensitive of their long history together, while also still respecting my needs. I was single for so long, I feel out of my depth. To be quite honest, I’m very insecure about that, and I’m jealous he had a partner throughout his twenties, and had the opportunity to have a wedding, and be married.

I can’t help but feel like Option B. Any advice is appreciated.

Sincerely,

Second-Best

Dear I’m Not Calling You ‘Second Best’ Even If You Named Yourself That,

Your letter is but one chapter in a very old story, where straight women are simultaneously pressured to seek marriage and children and shamed if they admit to wanting those things where anyone might hear them. Straight men in these stories tend to show up as intensive renovation projects who will be ready to “settle down” someday, it’s just that right now they are skittish wild stallions who might bolt at the first sign of anything like “human needs” or “priorities.”

The more we buy into that story, the more we end up with relationship patterns where women do a ton of work to “prove” their worth to men who may or may not have the bright idea, completely of their own volition without any prompting, to reciprocate someday. I think this is a fairly mild case*, but the reason I’m classifying your problem this way is that you are scared that talking frankly about future plans with a partner who seems to be making a lot of the same future plans will somehow “ruin” the relationship. If the relationship does not in fact survive a “Dude, when are you getting divorced?” conversation, it won’t be because your needs were silly or you asked for them wrong. For any advice I give you to actually work, we have to start here: You want to get married and have kids. You’d like to do that with J. You would prefer to start sooner rather than later. If he also wants those things to happen, then literally the least he can do is file paperwork that he’s had the last three years to do. If he doesn’t want that, waiting another year to find out is hardly in your best interest.

(*For comparison purposes, just as the sun rises and sets, we can trust that each new day will bring a new Reddit post about a recently-or-not-quite-divorced cishet man who expects endless financial and emotional support, housework, and even on-demand childcare for kids from previous relationships in the streets and offers nothing but eternal life in Casa Mojo Dojo with his Long-Term Long-Distance Low-Commitment Casual Girlfriend in the sheets.)

Since The Holidays are looming and we’re about to enter Year Four of him being broken-up-but-not-on-paper, I think it’s the perfect time to clarify some stuff. Start with sorting through your own fears and needs. Figure out what a good outcome looks like and what kind of boundaries and limitations you’d be comfortable enforcing. For example:

Is some of your insecurity and malaise being driven by family pressure? Is the prospect of 10,000 “So when are you crazy kids getting married?” “Hahaha I’ll let you know as soon as the divorce is final…or even filed…” conversations making you not look forward to running the imminent Celebration Gauntlet together? Is his limbo status causing you to feel like you have to lie to family members? What if you didn’t lie? Would it be better for you to fly solo this year and give him time to catch up on his paperwork and hang with his own family of origin instead of doing the Cute Couple Thing with this big missing piece still between you? (I know that feels like punishing yourself on some level, but I want you to at least think about it. When you brought him around in the past, it’s likely that you didn’t know that he was still going to be married for at least another year. Now you know. Does it change your calculus if you think about it as a respite for you from worrying about this vs. denying either of you something?)

It doesn’t sound like you live together, which is a good thing in my opinion, but are you talking about combining households, finances, DNA, etc. in the near future? Consider that if there’s been no legal separation, then it’s quite possible that your boyfriend and his ex are jointly responsible for any debts the other one incurs, listed as beneficiaries on all kinds of paperwork, and legally able to make complex medical decisions for each other in case of emergency. So maybe a bright red “Hmmm, that sounds like a great topic for after you’re divorced!” boundary needs to come into play before making any big plans. Speaking of which, if you can get pregnant, this is a great time to revisit and lock down your birth control situation so there are no accidents. Gestating Mr. Technically Still Married’s fetus is not going to make you feel more secure or in control right now.

Do you have an internal Sheelzebub Countdown running? Meaning, if you knew that this thing that makes you unhappy was unlikely to change, how much longer would you stay invested? Another six months? Another year? Longer? If you do have that internal counter running, maybe combine it with the boundary about discussing future plans, like, “Once I check in again about divorce, I’m not planning any joint vacations, purchases, family visits, merging of practical stuff with him for six months or he handles his shit, whatever comes sooner.”

Once you’ve reminded yourself of your own priorities, then I suggest being as frank as possible: “Hey, as we’re making all these plans, I’d like an update on how your divorce is coming along. As of July you still hadn’t filed, but how do things stand now?”

Where you go from there is going to depend on what he says and what you want to do about it. Once you bring it up, don’t be afraid to ask all the questions that are on your mind. (It’s not like it’s going to get less awkward, and more honesty and clarity might lead to good things).  If he hasn’t filed, why not? What is the barrier? What is his timeline and plan for resolving that? Is it financial, does it have something to do with the legal system, is it something that he needs to work out in therapy?  If they’re ‘working on it,’ what does that mean in practical terms? Is it his plan to move forward with you on stuff like marriage and kids? Does he understand that none of the stuff he talks about doing with you someday, like having kids, is remotely on the table until he handles this?

For best results, resist the urge to explain yourself. Your explanation is, “I love you, and I want to be with you and do all the great stuff we’ve talked about, but it’s hard to move forward with future plans while you’re still married to someone else.” You took a risk on him when you could have been like, “uh, I like you too, but howabout you call me after you’re all the way single” and you have nothing to prove to this guy about your open-mindedness or loyalty here. It’s been a year since you got together, and it is okay to want him to formally end his marriage before making any more promises or plans with you.You’re not being unreasonable, “nagging,” too needy, controlling, or whatever negative messages are bouncing around in your head. Don’t be afraid to swat down excuses and bad faith arguments like paper airplanes. “If it’s ‘just a piece of paper,’ and it ‘doesn’t change how you feel about me’ then it makes sense to ‘just’ file it already.” “I”m not ‘making a big deal,’ I’m telling you outright that it matters to me.” “Look, I’ve tried to be really hands off about this, but it’s definitely on my mind and I’m not a jerk for wanting an update.”

There is a risk that he will continue to stall, and if that happens you’ll have to decide what you can live with. By probing further, you may find out truths that you don’t want to. He may in truth not want to be divorced. Even if he does, he may not be on the same timeline as you are about getting married and having kids. He may be so disorganized that he’s a bad fit for you simply in practical terms. Is running the risks of big honesty and big love better than sitting with this dread and uncertainty for another year of your precious life? From here, saying “Are we really doing this? Then I need you to sort out your shit if you’re serious about being together” and potentially learning an answer you don’t want seems better than letting someone string you along, but only you can decide if that’s true for you.

Hi Captain!

My question isn’t life or death but it’s been on my mind. I have a group of friends whom I love very much and maybe it’s the Taurus in me but I’ve enjoyed giving them birthday/holiday gifts a lot over the years, usually small but meaningful items. Also, many times now, the group has come together to fund the purchase of a larger item for one of the friends – I’ve coordinated a few of such gifts myself (collecting from everyone, buying and wrapping the item, etc). 

My gripe is I haven’t been on the receiving end of any of the collective gifts ever since I’ve been friends with those people, even though I’ve pooled money and work into gifts for others many times. It’s also happened on several occasions that I arranged little gifts or handmade cards for everyone only to find out a few pairs of friends exchanged gifts but I wasn’t a part of any of them. 

We have a graduation coming up and one of my friends suggested we come together to buy the soon-to-be professional a good quality version of an important tool he’ll use in his new career. On one hand, I want to share in the celebration, but on the other hand, it makes me very sad and a tad resentful to think I’ll just once again participate in a thoughtful gesture that I’ve never been (and at this point might not ever be) on the receiving end of. I actually graduated myself during the pandemic and could hardly celebrate at all, which makes this all the more bittersweet.

I realize I could just opt out of this next collective gift, but everyone else is pitching in and I’m going to the graduation party – it would probably create a weird situation and I doubt my friends would get the message anyway. I think I need to say something to them, but how do I do that without being disrespectful of everyone’s finances and creating unfair pressure? Is there even a point in saying something? I feel like I’m basically saying “I don’t want to have to ask for flowers, I just want you to buy me some” but with my friends. It’s not that I absolutely want gifts, I’m just tired of feeling like no one thinks of me.

Thanks a lot Captain, 

Who Gives Gifts to Santa? (they/them)

Dear Who Gives Gifts To Santa?

Are there one or two friends within the group that you trust to a) successfully organize the logistics of a group gift in your stead and b) listen to your gripes about this without getting defensive or judging you and, c) possibly more importantly, without doing some stunt that escalates tension within the whole group? If you’re having a hard time pinpointing someone, is there someone who does a good job getting you individual gifts or, barring that, is a thoughtful gift-giver during 1:1 exchanges? The friend who suggested the most recent group gift seems like a good place to start.

What you want: To be included in everyone’s gift calculus the way you include them in yours. It’s probably more realistic to stay focused on what you want to happen from now on (vs. getting justice or guilty makeup-gifts for past omissions).

What you don’t want: To hijack your friend’s upcoming graduation gift to be All About You in a way that leaves a bad taste in everyone’s mouth and you still anxious and left out the next time it’s potentially your turn. A lot of times, attempting to engage the whole group about something like this ends up being the emotional equivalent of a passive-aggressive note in an office kitchen about how EVERYONE needs to make a new pot of coffee when they finish the old one (which the people who already make coffee will resent and the one person who doesn’t will go on blissfully ignoring). Which is why anytime someone writes in with a “me vs. a whole group ” social problem, I advocate starting one-on-one with the most reliable person first.

When you’ve identified your potential ally or allies, pull them aside for individual chats. This is where a phone call or in-person talk might serve you better than something that could be copied and pasted into group chats, and this is where (if you do use email) you don’t want to craft this as a response to any current gift-giving logistical threads in case of accidental forwarding.

Possible Script: “I realized that as we were organizing [New Grad’s Gift] that sometimes I forget to remind people about my own important milestones. My graduation was during the height of pandemic isolation, so I understand why celebrating wasn’t on everyone’s radar, and I’m sure a lot of people felt similarly melancholy about celebrating their own stuff alone during that time. But I don’t want to leave anyone out or be left out from now on. Since you’re also good at taking the lead on this kind of thing, could you and I make a pact that I’ll organize stuff for you and you can do it for me from now on? That way we won’t fall through the cracks.”

As for holidays, birthdays, and one-to-one gift-giving, I think when you’ve been friends for a while it’s totally appropriate to check in and say, hey, do we do the present thing for birthdays and holidays? Do we want to do it, if so is there a budget or type of present that would work best, would we rather just skip physical gifts and make plans to hang out together, etc.? Again, this is where asking people in the group who are more similar to you about organized gift-giving is probably going to yield better results. People just have different interests and capacity around this kind of thing. It’s also appropriate to notice if certain people never reciprocate your gestures and just quietly stop including them on your list from now on.

I actually love that you mentioned the common flowers conundrum, where people want to receive flowers but somehow it’s ruined if they have to ask for them. See also: Handwritten thank you notes for gifts. Birthdays where one person makes a giant deal out of birthdays hoping/assuming that other people will reciprocate and make the same kind of production when it’s their turn, but nobody does. These arguments always devolve into a “cut flowers are stupid, birthdays are stupid, postal mail is stupid, I don’t need those kinds of celebrations or gestures ergo it is irrational to expect me to provide them for other people” vs. “Yo, if it’s really important to people you care about, and it doesn’t harm you, perhaps assigning ‘most rational’ status to the one position where you never have to make an effort is not necessarily the best way.”

For people facing this advice column staple brand of problem, bottom line is, whatever your assumptions/hopes are about how a given relationship is supposed to work, whatever the lore says about good manners, if there’s something you need or want within a relationship and quietly modeling meeting that need for other people in the hopes that they’ll pick up on what you’re doing and reciprocate isn’t getting it done, you have other choices.

a) Say nothing and continue to stew in silence forever.

b) Stop doing un-reciprocated things for unappreciative people, though I would caution you that people who don’t really notice your thoughtful gestures in the first place may not receive this as the pointed message of protest or correction you intend. (There’s a reason that protests, boycotts, strikes are persistent, organized, collective actions with clear demands attached). If you let go of notions of punishment and justice or getting a particular response and view it as reclaiming your time and energy and possibly redistributing that to people who do reciprocate, it can be liberating for you, but it won’t change the other person’s views or behavior by itself.

c) Say something and give people a chance to respond and adjust. “How would you like to handle birthdays from now on? Birthdays are really important to me, so I usually prefer to do ________, is that something you could do for me? What kind of stuff do you like to do on your birthday?” “Hey, when I send you a present and I don’t hear anything back, it makes me feel like you don’t care. Well, first it makes me wonder if you even got it. Then it makes me sad. Do you want me to stop with the presents? Or could we agree on a 24-hour “thanks, I got it!” policy, even just a text?” “Hey, I love flowers and it would make me really happy if you got me flowers sometimes without being reminded or specifically asked.”

c) If speaking up doesn’t get you what you need, start looking for other ways to meet those needs and balance the relationships. Buy yourself flowers. Throw your own birthday party, and/or shamelessly remind the people you expect to care when your birthday is coming up.

My lovely Letter Writer, it sounds like maybe you need to celebrate your own graduation right now, even if it doesn’t involve the exact same kind of group gift your friend is getting. Maybe you need to buy yourself a present. Maybe you need to throw a party. Maybe that party can be a collective thing where you tell your group of friends, “Hey, everybody who had a big deal event during 2020-21 that would normally involve balloons and opening presents, let’s do Graduation, Etc. (Observed) on [date] at my house. Off the top of my head, I got my degree, [Name] gestated an entire person, [Name] got a big promotion, [Name] bought their first house, [Name] published not one but two poems, who and what am I forgetting?”

I used to* have two local friends with birthdays the same week as mine, and together we formed the A.S.A.M.A.S. (Aquarius Self-And-Mutual Admiration Society) where we gave each other elaborate birthday greetings comprised of equal parts bragging about ourselves and complimenting each other. “Birthday felicitations! I am looking amazing tonight, as are you!” “Have I told you lately that I extremely cool and that you are lucky to know me? You are also quite nifty, what a privilege it is to know each other!” “Oh my god, what a brilliant observation I just made! And your joke was the cherry on the excellent sundae of my wit!” (*Used to as in I still quite like these people, we’re just not local to each other anymore.) We played D&D and similar games together, and whatever our character sheets said we were all bards to the marrow in real life, so every meeting of the A.S.A.M.A.S. had the same goofy, over-the-top energy as ” Matt Berry reading dril Tweets” or this scene from Booksmart (except you have to imagine that everything they say to each other, they say about themselves first):

I include this anecdote to say that you’re not being whiny or ridiculous for wanting to be celebrated by the people you love as much as you celebrate them. And whatever the etiquette guides say about it being rude or needy to ask for gifts, you’re not silly for wanting validation and safety and appreciation. Stuff falls through the cracks sometimes, and we all need rituals to remind us of what’s been lost and how to put our relationships back together. Maybe those rituals can start with giving ourselves some generosity and love before we give it all away. So here’s wishing you some version of the Taurus-Thoughtful-Gift-Exchange-And-Appreciation Society before another year goes by. Possible template: “Hey, for [Insert Occasion], howabout we each get ourselves something we really want and we’ll wrap them and give them to each other, open them, and then immediately switch back so we end up with our own original gift? Then we can be like, ‘HOW THOUGHTFUL, IT’S EVERYTHING I WANTED.’ ‘YOU ALWAYS KNOW EXACTLY WHAT I NEED.’ ‘OMG I HAVE NEVER FELT SO SEEN.'”

Announcement: the audience for these has changed, so I’m going to do them once every three or four months instead of monthly. So please come to this October one if you’re interested, there won’t be another until probably January or February.

21st October, 1pm, Royal Festival Hall, Southbank Centre, SE1 8XX.

We will be on Level 2 (the upper levels are closed to non-ticket-holders), but I don’t know exactly where on the floor. It will depend on where we can find a table. I have shoulder length brown hair, and will have my plush Chthulu which looks like this:

Please bring your masks/exemption lanyards, and obey any rules posted in the venue.

The venue has lifts to all floors and accessible toilets. The accessibility map is here:

The food market outside (side away from the river) is pretty good for all sorts of requirements, and you can also bring food from home, or there are lots of cafes on the riverfront.

Other things to bear in mind:

1. Please make sure you respect people’s personal space and their choices about distancing.
2. We have all had a terrible time for the last four years. Sharing your struggles is okay and is part of what the group is for, but we need to be careful not to overwhelm each other or have the conversation be entirely negative. Where I usually draw the line here is that personal struggles are fine to talk about but political rants are discouraged, but I may have to move this line on the day when I see how things go. Don’t worry, I will tell you!
3. Probably lots of us have forgotten how to be around people (most likely me as well), so here is permission to walk away if you need space. Also a reminder that we will all react differently, so be careful to give others space if they need.

Please RSVP if you’re coming so I know whether or not we have enough people. If there’s no uptake I will cancel a couple of days before.

kate DOT towner AT gmail DOT com

Hi Captain! 

My best friend of over a decade and I live several states apart, and last week she and her boyfriend came to visit me and my husband. They’ve been together for nearly a year, but this is the first time I’ve really interacted with him for a long period of time.On this trip I have been confronted with the fact that they are an incredibly annoying couple to be around. They spent about 50 percent of the time we were together having one on one conversations that me and my husband were not included in, including in spaces where we couldn’t get away or do something different, like when we were all driving somewhere together. They are sugary sweet romantic — calling each other baby/dear/etc constantly, constantly complimenting each other and calling each other hot, TONS of PDA (like to the level where they will be standing next to us, totally ignoring us, and borderline making out). They both seem to be putting on a kind of weird persona with each other that isn’t their actual personality, as if they are “on their best behavior” (I can’t say for sure for him, but I got that vibe. For her, it was a weird version of her I’ve never seen before).

They were also really disrespectful of our time. For example, they cancelled an outing with us — that we had planned weeks before — as we were walking out the door to meet them, because they “wanted time alone” (this trip was allegedly to visit us?). Similarly, one night they showed up over half an hour late to our dinner reservations and didn’t apologize or text to tell us they were running late. They have big “new young couple energy,” but it’s been a year and we are in our 30s. I honestly don’t have any sympathy — I thought the whole thing was rude as hell. I didn’t say anything about it initially to my husband because I wasn’t sure if I was just being jaded, but he brought up how uncomfortable he was without me even saying anything.

We also all got dinner with a mutual friend and he texted me after to say, essentially, “what the hell was all that about?” They had pretty much ignored him for the entire dinner and only spoken to each other. When he said goodbye, they didn’t even look up from cuddling each other. I’m at a loss as to how to move forward. Frankly, I’m confused because I think that all of this (the lateness and flaking, the constant PDA, the one on one conversations in front of us) is really unlike her. She didn’t seem like herself at all, and I couldn’t believe she was treating us like this. It was also disappointing to think I was going to have a fun trip with my best friend, and instead get flaked on and ignored the whole week. I also have some light concerns about the partner. It worries me that I feel like he’s putting on a persona, and the obsessive vibe of this relationship gives me pause. I don’t know what, if anything, to say. She is head over heels in love and sure she is going to marry this man. I don’t know how to address this without putting the friendship in jeopardy. 

Thanks,

Not Feeling The Love in California 

Dear Not Feeling The Love,

My sympathies! I have been at what I thought was a gathering of friends and our various romantic partners that turned out to be two people on a hot date with the rest of us as background characters and it was ungood for all the reasons you describe. The part where it all feels like a performance is the worst for me, and it gets even worse when the new relationship energy wears off and the performative foreplay turns into performative arguing and now everyone is trapped in an amateur production of Who’s Afraid of Virginia Woolf? for the rest of the night. It’s been a while since anyone has inflicted this particular horror on me, personally, but I well remember the glazed expressions of my fellow NPCs around the dinner table and my own internal screaming. “Where even is my friend right now? Does she know that we are here? Is this happening because we are here to see it, or are they like this all the time when they are alone? Which of those is worse to contemplate? If I slip out and go home, will they even notice? If say something, will it make it even more awkward?”

I would love to tell you that I figured out a snappy way to shut it down, obtain anything resembling accountability, or relay concerns about a relationship that required so much performance while it was still happening, but I never did. In the moment, there was always something happening under the surface that wasn’t really about me or the other bystanders. Something that went beyond being naturally demonstrative and affectionate, something that was about proving something to somebody. The nature of the “something else” varied from friend to friend, partner to partner, and setting to setting. Occasionally it felt like people who had been single for a long time while surrounded by happy couples were trying to stake their claim to something they’d felt excluded from. Other times it felt like people were picking fights in public that they didn’t feel comfortable having in private, taking advantage of safety in numbers. Troubling! Sometimes they just loved me and loved their new partner and really wanted us to love each other and to bask in validation and togetherness on all sides. If it was a matter of introducing a new partner to a group of friends, if I squint I can see it as overcompensating to make sure the partner doesn’t feel left out. Alcohol may have been involved. These are all conjecture on my part, but the worst instances shared a level of demonstrativeness and inattention to surroundings/me/other people that crossed a line, even if that wasn’t the intention, and an unfortunate tendency to double down if challenged because any attempt to wrest the couple’s attention away from each other posed a threat to whatever underlying doubt or need required that kind of proof.

Truthfully, I think your options are limited here, especially now that the trip is over. It’s like in the original Darth Vader Boyfriend post where your friend is getting something that you can’t see out of whatever this is, and she’s unlikely to want to hear anything you have to say as long as she’s still dickmatized in thrall to that thing. To be clear, I don’t think any of your concerns are misplaced, or that you aren’t within your rights to call your friend up and say, “What just happened?” or think that her partner is off-putting in the extreme.You know her better than I do, so if I’m wrong to be skeptical, definitely reach out in whatever way you think might work. “Can we talk about the trip? I was really looking forward to seeing you, but at times it felt like I was interrupting a romantic vacation with your boyfriend and other times it felt like I was watching the Best Friend-Boyfriend show. I’m so happy that you are happy, but next time can we [plan some stuff for just us][set some PDA ground rules][draw clearer lines between romance time and friend time]?” Do I think that conversation will go well? No. Does that stuff maybe need to be said anyway? You’re the only person who knows the answer to that. In the meantime, let’s discuss other options.

First, whether you and your friend hash this out or not, you’re certainly never doing that again. You can’t go back in time, but you can change how you prioritize and plan in the future. Now that know that your friend’s boyfriend cannot hang, or that she is unable to hang when they are together, or some combination of those things, you should remain leery of scheduling any double dates or group dinners or intruding on their romantic getaways in the future. Try to look at the night they cancelled “to be alone” as a gift, and use that same logic for carving out quality time for just you in the future.”Instead of everyone meeting up, why don’t you enjoy a nice date with partner tonight, and then you and I can go out tomorrow and really catch up?” “Why don’t you and me just go for a long weekend somewhere, no boys allowed?” And if you ever do end up in the same situation again, hopefully at least you and the other flabbergasted dining companions will  be more equipped next time around to embrace side conversations and tag-team on the occasional “Get a room, you two!” “Is this a private conversation or can anybody join?”

That’s what I did to maintain friendships while minimizing my own exposure to any Dinner-And-A-Show dynamics. I enthusiastically planned things and RSVP’d to anything where it was just me and my friend(s), and absented myself from anything that wasn’t. That became the new default setting, with rare exceptions for special events like birthdays and weddings where putting my foot down to make a point would make me the jerk. I figured I can get along with almost anyone for a couple of hours, and maybe after repeat exposure some of the novelty of “Nobody Has Ever Been This Much In Love Before!” would wear off and everyone could chill out. Other times, I hid behind wanting advice about my own personal stuff or arranging activities I knew that the partner would absolutely hate* to try to carve out a little privacy. And I thought a lot about venues that set everyone up for a good time. If booze or other substances repeatedly brought out the worst in certain people, then I would plan to see them when everyone was more likely to be sober. Since I’m a person who doesn’t really enjoy altered states, I could blame it entirely on myself and my own preferences. I need an early night. I would rather do lunch than dinner. Order whatever you want, but I’m not drinking today.

After seeing the same cycle repeat itself more than once, I also learned to give it time. Even if I was annoyed and felt ignored at times, I wasn’t going to end important friendships over this. Over time either a person I loved would be so happy that I could ignore the occasional oxytocin chemical spill for their sake, or they would break up with the human velcro and it wouldn’t be a problem anymore. I also learned that even if I spotted red flags correctly, if led with judgment and advice when my friends were head-over-heels and thought things were good, they would be less likely to come to me when things were bad. So I tried very hard to let go of the need to be right about their lives and focus on my own boundaries. I didn’t have to argue or fix anything. As long as I could engineer hangouts where my friends and I could be fully present with each other most of the time, then their romantic dynamics could be their business most of the time.

When conflicts arose, I tried to find something honest I could say that kept the focus on myself and not an implied judgment of the relationship or my friend. “It seems like you never want to do anything with me and Partner!” “That’s fair! I get to see you so little as it is, so when I do I selfishly want you all to myself.” “But I do stuff with you and Mr. Awkward all the time!” “That’s true! But if you ever want to hang with just me, I’m happy to set that up.” (I left out the part where he and I don’t wear each other like a sweater when we go to restaurants.) Sometimes a more direct challenge arose, something that teetered close to truths that nobody wanted to admit. Trouble is, I can’t not admit those things once someone says them out loud, so I aimed for a breezy joking-but-definitely-not-joking assent. “You’ve never liked Partner!” “If you say so! I do know that you tend to be pretty caught up in each other, and I’d rather not intrude on any more of your dates.” “We’re not like that! You just don’t want me to be happy!” “Sure, that must be it. Anyway, let me know if you, singular want to grab breakfast tomorrow.”

I don’t know if any of this is helpful as advice, but you definitely have my commiseration and hope that things will get easier over time.

*Incidentally, the 2004 micro-budget horror film Fear of Clowns **which is at this link you should NOT click** is terrible, and I don’t recommend it unless you can cackle through it with your best friend while her terrible (now-ex) boyfriend hovers in doorway of the room you’re watching it in for 106 minutes straight, fuming about how bad it is even though you both told him ‘yes, we are watching bad movies on purpose’ and ‘you will definitely hate this’ and ‘we rented it to watch together, there is no need for you to stick around’ but his rarified media tastes and even more intense FOMO simply will not allow him to either sit down or leave and do something he enjoys instead. The more we laughed at this convoluted tale of a homicidal clown named Doug who never wears shirts and only refers to himself in the third person (“Doug take murder van?”), the more he fumed. The more outraged he became, the funnier it was. Someone so transparently pathetic should have been way more used to the derisive cackling of women, in my opinion, but I’m sure the seventeen years since I last saw his squinched-up rageface and flaring nostrils have afforded multiple opportunities for growth on that front. Cheers to a complete toilet!

**You clicked the link, didn’t you. And you glimpsed “Doug” in all his shirtless not-glory. Well, now you know. Happy almost-Halloween!

.

Dear Captain,

Thank you for telling me years ago (in an unpublished letter) to dump my boyfriend. This one may be tougher.

When my best friend, “Leah,” and I met, we were both in our charmingly messy mid-20s, full of joie de vivre and liquor. It was one of those friendships that felt like we had always known each other, and we bonded really closely despite ultimately having a long-distance friendship. We text almost every day and have flown to see each other at least twice a year ever since. She is so funny and interesting, and we’ve always based our friendship on not judging each other, but it’s getting harder for me to hold up my end of that.

It’s been almost a decade, and Leah and I have been growing in different directions. Or, from my perspective, I have been growing, and Leah hasn’t been. She’s still partying all night, getting fired from a series of jobs, and having what feels like middle-school drama with friend groups and the people she dates. She’s still running into the same life-disrupting stuff that happens in early adulthood, like when you don’t know how to book a doctor’s appointment so an infection festers, or you have to cancel a trip you planned because you didn’t renew your passport. Her main interests have become astrology, reality TV, and partying. Her primary ambition seems to be TikTok virality. It often feels like I’m listening to a teenage niece talk about her life instead of a peer. I’ve never told her to do anything differently — we’re not supposed to be judging each other! It’s HER life! — but I just keep thinking, dude, grow UP.

Her choices aren’t objectively or morally wrong, but I’m just in a different part of life! I’m interested in the “boring” “grown-up” stuff now! I have a marriage (which I rarely talk about with Leah, because her default response to any conflict with a partner is “well, just break up with them” or “lifelong monogamy isn’t realistic”), and a demanding but rewarding (unglamorously corporate) career, and now, I’m having a baby. I am so psyched about this baby! But I’ve been dreading having to tell Leah, because I am afraid that once the baby enters the chat, we won’t be able to pretend we’re compatible any more.

Leah has expressed MANY times that she never wants kids, that she hates how her friends who have kids can’t party, kids are gross, etc. I have never said to her “Hey, that makes me sad, because I want kids,” but I’ve talked about wanting them. One time she angrily vented to me about her friend who had just gotten pregnant before her wedding, because it meant they couldn’t do “anything fun” for the bachelorette “or ever again basically.” And since then, she’s kind of dropped that friend! I have no idea how she’ll take it when I tell her. I hope she’ll be happy for me? I hope she’ll stop saying stuff about how kids mean your life is over and how they wreck your body and make you lose your whole identity? I hope she won’t be mad I didn’t tell her I was trying to get pregnant. I hope we can find a way to talk about how we’re at really different places in our lives and we still love each other but there’s less and less that we have in common.

I’m not sure if I’m asking “how do I tell my anti-kid Peter Pan friend that I am permanently leaving Neverland” or if I’m asking “can this friendship survive this baby and/or is it already dead” or “am I an asshole who needs to have more patience for a really good friend who is just making different choices than I am” but hoo boy, I need some wisdom.

Anxiously,

Ticking Time Bomb Uterus

Dear Time Bomb:

Congratulations on your good news, I am so happy for you! And thanks for the addition to the “Dummmmmp Himmmmmm!” happy ending file.

It’s very possible that your friendship with Leah will not survive this news or the big changes ahead. You were outgrowing the friendship even without this, and she’s made her views very clear in the past. If she reacts unpleasantly, as if this is something you are doing AT her, or drops the friendship altogether, then that is certainly her choice. But before you blame yourself or the bundle of cells and possibility you’re incubating, remember that Leah has the same opportunity to show up for you in the ways that make sense for her that you’ve been doing all along as your paths have diverged. So when you tell her your good news, I want you to think about it as good news (because it is) and as a gift to her in the form of a chance to rise to the occasion.

Postal mail is your friend here. You can organize your thoughts in a card, send it off, and not really think about it until she answers. Leah can have her initial reaction in private, and then decide how she wants to respond to you. It probably beats watching three dots appear and disappear again in a text message window and sharply reduces the risk that anyone will blurt out anything they regret. And if you do put your news in a letter, you can also include your honest fears about her reactions and your hopes about what happens next.

Sample:

“Dear Leah, I have some big news: I’m pregnant, due around [date]. I’m a mix of overjoyed and nervous, like every prospective parent. One of the things I’ve been nervous about is telling you, which is why I have held off until now.

You’ve consistently been very vocal not just about remaining child-free yourself (which I completely support!) but also about distancing yourself from friends who made different choices. That’s also up to you, but it makes me sad to think about potentially losing one of my favorite people. I have zero expectations that you’ll suddenly become interested in babies or toddlers, the same way that I have not so far become a TikTok trendsetter or amateur astrologer, but we’ve managed to stay friends this long despite our lives being very different, so is it silly to think we could find a way? Things are going to change for me, very rapidly, but down the road, I like to imagine girls’ weekends away from the kids and perhaps even Cool Aunt Leah advising my surly teen about being a [Star Sign] and knowing the difference between fun bad decisions and the kind that are just bad.

If that’s something you can picture too, then what I need the most right now is for you to hold off on the kind of comments you’ve made in the past about kids being gross and ruining lives. You don’t need to come to any baby showers or fake enthusiasm, but I do need you to keep that kind of thing to yourself around me from now on. Even when it’s a happy choice, pregnancy is hard, and the last thing I need is to be treated like I’m wrecking your life somehow by living mine. I hope I’m wrong about your potential reaction and that you’ll find a way to be happy for me.

At least by putting all this in a letter, hopefully you’ll have a minute to whine to your fun friends about how I’m joining the Pod People and get it out of your system before we talk, at which time you can say normal stuff like ‘Is it true pregnancy makes you have to pee all the time?’* and ‘You aren’t going to give it some dickhead name like [Worst Ex Ever] or [Celebrity Crush] or [Erstwhile Nemesis] right?’**

Talk soon,

Ticking Bomb”

*Yes, it’s upsetting.

**Prospective names are top secret between me and [Spouse] until there is an actual baby, but if you’ve kept a good list of dickhead grudge names we should definitely not use, please send it along. I trust you especially to think through the potential nickname pitfalls that could arise on the playground.” 

As always, adapt and discard anything that doesn’t work for you. You may not want to go into this much detail in whatever you send (“Hi Leah, I’m pregnant and I need you to not be an asshole about it. Cheers!”), but I figure that if you’re worried the friendship is going to end anyway, you lose nothing by being very honest about how you’re feeling and what you want to happen. Plus, it’s not like her past views are a secret! There’s nothing unkind or unfair here as long as your musings on her relative maturity levels and choices remain between you, me, and the rest of the Internet. The perfect letter is not going to fix anything that’s already broken or suddenly make her into a different person, but sometimes the kindest thing you can do is give people a chance to pleasantly surprise you and enough time to find out.

Again, I send you all the congratulations and hope for the safest and easiest possible ride. And I hope you are surrounded by people who are excited to show up for you even if they don’t have 100% of everything in common. Some of my favorite people made small people, and no identities were lost in the process.