User blogs

Dear Captain,

My current workplace (where I have been working for about 18 months) is the first place I’ve ever worked where I feel like I can come close to being myself. I have interests in common with my colleagues. For the first time…probably ever I am not the weirdest, most socially inept person in every room I enter. It’s nice but also very, very confusing. I don’t know how to be friends with people I work with. I also don’t use social media, so I can’t just send a casual friend request to create a connection with a colleague that exists somewhere other than the lunchroom. That’s all fine, I see these people almost every day…but now my favourite colleague is leaving to take a permanent job in another state.

I’m disproportionately upset because I haven’t made a new friend in over a decade, and I really enjoy this person’s company and was hoping they would eventually become a friend outside of work, not just a colleague. Everyone I am friends with now is an offshoot of the group of people I hung out with in college. I… don’t know how to make a connection with this person that will survive them moving to the other side of the country. Maybe it’s impossible. Maybe if they wanted to actually be friends they would have indicated that somehow before now – although I’m not actually sure I would recognise it if they had. What can I say that invites them to stay in touch and conveys the fact that I’ll miss them, without sounding like a stalker in the making? Yes, with no exaggeration, I am genuinely this socially clueless.

Yours, 

Workmate 

Dear Workmate,

The “what to say” is the easy part. Acquire a blank greeting card with an image you like. Write something similar to this inside it, give it to your coworker on or around their last day:

Dear [ColleagueName]:

Congratulations on your new job, and best of luck with your move!

I’ve so enjoyed working with you and getting to know you during the past year. I don’t use social media, but if you’d like to stay in touch my phone number is (xxx) xxx-xxx and my personal email is [address]. Please don’t hesitate to get in touch if you’re ever in town and want to catch up over coffee or lunch sometime, and of course I’m always happy to be a work reference should you need one.

Very best wishes,

Your Name”

Another way to do this is to ask, out loud. “I’ve really enjoyed working with you and would love to stay in touch after you leave, can we trade contact info?” Then you offer yours and let the chips fall.

Neither of those strategies are remotely stalker-ish. They both involve expressing genuine appreciation and giving your colleague a way to get in touch should they wish, and then leaving the ball in their court to reciprocate. If they reach out, it’s because they wanted to, and if they don’t, oh well. Once you supply the info and say something nice you do not have to do any more work about it ever again.

Now for the medium-bad news: You are probably right that that the timing is not great, as interstate moves are not exactly conducive to building close friendships from scratch with former colleagues. Even if they seem favorable to the idea of staying in touch, I would not count on your soon-to-be-ex colleague making *any* effort until well after they are settled, at which point a realistic “win” here is that you stay in touch as professionals within the same field who interact very occasionally. “I saw this job posting and thought of you.” “Did you see this neat article about [your area of expertise]?” “Are you going to the conference next month? If so, let’s grab breakfast!” If you don’t stay in touch even to that degree, it’s very unlikely that it’s personal or because you did something wrong. Life happens, and even close friendships can founder when the proximity or other shared context that brought people together goes away.

So here’s what I suggest: Once you give your contact information and pleasant parting message to this person, it’s time for you to work on the overall skill of making new friends as an adult. What is it that you like so much about this person? Do you have shared interests or hobbies, a shared senses of humor, shared ethics or a shared approach to life? Other than work, where might you meet people who enjoy the same things you do and who remind you of this person? Is it time for you to try out a new class, volunteer gig, or shared hobby that will bring you into proximity with new people?

At work (or after work, more precisely) since you share common interests with multiple current colleagues, could you join in with ongoing social events or initiate some of your own? “The film festival is coming up, who wants to go in on a pass with me? This way we can get advance tickets to stuff and go after work.” “I’ve pledged to actually use the company gym membership this year, but I’m slow getting started. Any other rank beginners/casuals want to join forces on Tuesday & Thursday nights? That’s when I’ll be there.” “I’m going to sign up for this class in [skill we use at work] next month. Anyone want to join me?” To keep invites as low-pressure as possible, tell people about a thing you plan to do anyway and invite them to join you if they want. You’re participation doesn’t depend on them, it’s just something that might be nice to do together. And for best results, don’t think of it as you vs. the entire group. It’s okay to play favorites here and start with the friendliest people. Additionally, if your office or college friend group or newfound social hobby has one or more outgoing people who like planning stuff, I suggest cultivating the heck out of them and making your desire to be more social explicit. “I’m trying to be more social this summer. Any ideas for cool local stuff to do?” “This was such a great event, thanks for all your planning efforts. Next time, can I help?” “I don’t know anybody here, would you mind introducing me to someone?”

Next, it’s great that you have an existing friend group inherited from college, and you could probably do worse than put some love and appreciation into those relationships as well. Who is your favorite person within the old gang? When was the last time you did something fun, just the two of you, that didn’t require a giant group text and multiple calendar invites first?  Commander Logic (aka The Best Friend Who Ever Friended, Who Also Uses Social Media Lightly Or Not At All) swears by replacing most small talk openers with the question “What are you nerdy about lately?” and letting people share their excitement about something they like. This works equally well on new people and people you’ve known forever and assume you already know everything there is to know about.

People who write to me because they do not have the quality or quantity of social connections they wish they had are often carrying a lot of fear, anger, and anticipation/memory of rejection along with them. They wonder if they are permanently broken in some way. They’re very quick to tell me about all the times they reached out and nobody reached back, and use that as evidence that nobody will ever want to be friends with them and there is no point in ever trying anything else. They resent having to be the one who takes initiative and face rejection again and again from people who seem to have it all figured out. These folks have their own histories and good reasons for feeling the way they do, and a lot of it depends on the luck of who happens to be around them at any given time, since “Am I unhappy because I’m uniquely terrible or am I just surrounded by assholes?” is a question that will sadly never go out of style. I neither can nor want to invalidate these experiences, but the fact remains that there are basically five ways to make friends as an adult:

• Join stuff that you think you’ll enjoy and see who else is around. You may not make a friend, but being around people in a non-pressured way is good practice.
• Invite people you like to do stuff with you and see if that is enjoyable.
• Put yourself in the hands of your friendly neighborhood extrovert, show up wherever they invite you, and see if that is enjoyable. (Contrary to high school and common media tropes, people who love to plan social events and connect people with others are mostly not doing it in order to be as mean as possible.)
• Cultivate deeper relationships with people you already know and like and have stuff in common with….by inviting them to do stuff with you and seeing if that is enjoyable.
• Keep doing one or all these things until something clicks, which is less about your performance than it is about the luck of finding other beautiful weirdos who share your beautiful weirdness.

Just like with any other type of love, there is no secret shortcut or way to both remain permanently safe and invulnerable and have close friendships with others. Fair or not, if you’re the one who wants things to be different than they are, you’re going to have to take the initiative to change it. Beyond a) the reminder that social anxiety is a very common, treatable thing, and if you think you might have it it’s worth finding out for sure (even if just to rule it out) and b) the fact that once I learnedI was neurodivergent in my 40s it suddenly made sense that many of my strongest and best connections were with fellow neurodiverse folks, if I have One Weird Trick for people entering or re-entering a social scene in search of more connection, it’s this:

Do your best to be polite, curious, and gentle with other people, but beyond that, replace “trying to be maximally likeable” in new social situations with paying attention to your own pleasure and comfort.

Do they like you? Who knows? “They” are not a monolith and liking is completely subjective. Focus instead on whether you like them. Who makes you feel good, appreciated, welcomed, and valued? Who invites you in and rewards your effort to connect? What spaces feel welcoming and safe for you? Pay attention and seek those out. When you stop having fun, go home. That’s not a failure, it’s a decision to take care of yourself, and you can always try again another time. Conversely, who makes you feel judged, ignored, or like you are always chasing them or intruding? Who makes you feel chronically uncool and behind the beat? What spaces make you feel like an unwelcome visitor from another planet or like you’re wearing itchy shoes that don’t fit? Be polite when forced to encounter them, but stop making extra effort to fit in or minimize your own discomfort. That discomfort is trying to help you get the heck out of there and go somewhere fun *for you.*

The kind of persistence that’s so often sold in dating and social skills advice is full of hacks for turning people who don’t like you into people who do and making yourself into a person who fits into generic environments, like that’s some kind of prize. The only kind of persistence that’s ever worked for me is the version where I licked my wounds whenever something didn’t work out and then kept looking for people and places that required no convincing to welcome me in. My social skills, such as they are, improved 1000 percent once I stopped trying to fit in with people who just weren’t interested in the same stuff as me and when I stopped trying to get people who radiated indifference or dislike to stick around in my life. Turns out, the more I like where I am and who I’m with, the more likable I am.

You’ve finally found some people that you enjoy being around at work, and while one is leaving, the rest are not. Please don’t spend so much effort chasing the person who is leaving or running yourself down that you forget to appreciate the ones who are sticking around. What could be possible if you let go of the story that you’re bad at making friends and told a new one about finally finding out where you belong?

Dear Captain,

I (she/her, 30s) have been with my husband (he/him, 30s) for ten years now. We both enjoy traveling and we used to do it a lot more. I’m a freelancer who has always maintained a very flexible schedule and my husband’s job used to offer him a great deal of flexibility, too. Since we have no kids (and no plans for any), it was easy to take longer/more spontaneous trips. However, while the pandemic undeniably threw a huge wrench in our getaways, now there’s a different hitch.

My husband changed careers right when things slowly began reopening, and we basically haven’t traveled since. In his current job, he doesn’t have as much PTO as he did previously and it’s much harder to take more than a week off consecutively. I feel churlish complaining about this, because it’s the career path he’s wanted for a long time, that he’s worked hard to achieve, and that he’s very good at and well respected within. But travel used to be such a fun part of our relationship together. A good example of this is the two-week overseas trip we planned that got scuppered by COVID and still hasn’t happened four years later. I keep looking up itinerary ideas for that huge trip, or looking at old travel photos, or investigating new places to go, and then sighing and closing the window.

I know I shouldn’t let this fester. Our relationship is otherwise great, and I’m trying to find modifications like day trips or staycations, but it’s not the same. When I look at those old plans, which are now wildly out of date, I can’t help but have the thought that, by myself, I could have taken a trip like this every year. It’s a poisonous thought, and I recognize that. But I’m grieving part of our relationship that I loved.

He misses traveling, too, but “quit the job you love and find something less fulfilling so that I we can travel more” is a hell of an ask from a spouse.

What can I do to make peace with the life we lead now instead of the life we used to have?

Thanks,

Grounded

Dear Grounded,

It’s time to pull out a calendar and plan two trips. Vacations are like student film shoots, weddings, family reunions, moving house, and asking people on dates in this way: All agreements to participate, no matter how enthusiastic, are conditional until there are specific dates attached. Asking people if they want to do a thing in theory is not the same as telling them when you’re doing the thing and inviting them to join you at a specific time and place. If you start with a time you know works for you, you can negotiate as you go, but the longer you wait to find the magical perfect time when everything and everyone is available, the more you increase the risk that no one and nothing will be available.

The first trip is a joint vacation. If two-week blocks are hard to come by, then what’s a destination that makes sense for a week away within the next year? If your husband can’t go now, and he can’t go soon, then when *precisely* can he go? He’s been there long enough to know when the busy periods are and have a sense of how to budget his leave time, and the further in advance he books his vacations the more time his employer will have to plan. If he lets his job decide when he’s even allowed to ask for time off, he’ll never go, and if you wait for him to wait for them, you’ll never go. Plan it now.

The second trip is a solo journey or one you can take with a good friend or family member. You have a flexible job and a strong desire to travel. You have information that your husband’s schedule and priorities don’t allow him to accompany you like he did before, and you have information that if you wait until he is free, you’ll never go anywhere. What do you want to do with that information? You identify it as “a poisonous thought” that you’re trying to talk yourself out of, but why? Your husband may be your favorite traveling companion, but where is it written that he must be your only one for the rest of time? The subject of your email was:”How much resentment is too much resentment in a marriage?” Meaning, you already resent him. While the ideal amount of resentment in a marriage is probably close to zero, if there’s no way for everyone to get everything they want, why should the status quo mean it’s you who loses out every time? Would he resent you for going without him? If yes, is that better or worse than whatever is happening now?

You can’t go everywhere together like you originally planned, and you can’t expect your husband to give up a fulfilling career to roam the world at your side, so what can you do to get more of what you need? Start with two vacations and see how you feel.

Content note for body policing and mentions of BMI and specific weights, which I would normally redact with prejudice but I am leaving in this time because they are evidence of what an absolute non-issue this guy is escalating into an issue. To be clear, this would be a husband-problem with *any* numbers of *any* size, but just like the guy who had seven or eight investment cars, sometimes real numbers do bring home the absurdity of a situation.

Hey Captain,

I’m a 32-year-old woman married to a 34-year-old man. We’ve been married 4 years and have a beautiful 2 year old. For our whole relationship, my level of physical activity has been a problem topic. My husband is very physically active. He used to play soccer (had to stop due to an injury), walks, bikes, hikes, etc. When we met, I also was reasonably physically active, but doing totally different activities (yoga, dance) 1-2× per week.

We got married during COVID and I got pregnant relatively quickly. During pregnancy and since we’ve had our baby (now active, running-around-all-the-time toddler) I admit my physical activity has dropped to just functional things like childcare and walking around and running after our kid. I’ve done the odd dance workshop but am definitely not doing any regular scheduled exercise each week. I am of average weight (BMI in normal range) and am net 8 pounds heavier than I was when my husband and I met. In the 4 years we’ve been married, besides pregnancy and postpartum, I’ve also had another minor abdominal surgery.

Every few months, my husband and I will have a conversation in which he expresses that he’s quite upset that my level of physical activity is so low, and that he wishes we were doing more active things together. Ideally, he’d love to hike more together. Hiking has never been an activity I’ve enjoyed, and since we’ve been married my husband hasn’t been hiking much either although he used to do a lot more of it before (multi-hour, several-mile, strenuous hikes). A couple weeks ago, we had this conversation again, and he said if he’d known this is where we’d be 4 years after marriage, and if he’d known this would be my baseline level of physical activity, he would have reconsidered getting married.

My reaction was that (1) I am healthy and normal, and not on track for any kind of adverse outcome due to my health, (2) we have a good relationship other than this one point: he’s a great and involved dad, we live in a beautiful place in a house we love, and I bring a lot to the table (make as much if not more money than him, great mom, loving and caring and kind to him).

His reaction was that being of average health isn’t enough — his expectation in a partner is that they be of above-average health and activity, and he’s not willing to reconsider that, but he does want to work on our marriage and relationship. He reiterated that it’s not about weight for him, and that while he’d love a hiking partner he’d also just love for me to do whatever I want to do, as long as it’s some level of exercise ~3-4 times per week. Our sex life has been dead postpartum, and I think it’s due to this.

For my part, I agree that I used to do more when we met, but it doesn’t seem right that there’s no allowance for the fact that in the 4 years we’ve been married, it’s been COVID, pregnancy, postpartum, and another surgery for me. I do wish I was more active (I’m able-bodied and am physically able to do more than I typically do each week) but I don’t honestly know what’s stopping me. I’m also worried I won’t be able to meet my husband’s standards even if I tried. Our marriage feels like it’s on the rocks, and my self esteem is really low at this point. Where do we go from here?

Hello, thank you for your question, and I’m sorry you married someone who has chosen to be #ThisFuckingGuy for the time being.

If your husband is telling the truth that he married you under the assumption that that you would transform into a different person who liked all he same things he liked, and he’s been waiting all along for you to magically mutate, that is a him-problem, not a you-problem. Maybe he should talk to a counselor about why he is having so much trouble letting go of his unrealistic fantasies and why he’s making you responsible for fulfilling them. If this is about his fears about your mortality after some serious health issues, a counselor can help with that, too.

If your husband is anxious about his own activity levels post-injury, post-COVID, post-baby, etc. then maybe instead of blaming a person who has never been interested in hiking he should join a hiking club for men or make some friends who hike or call up his old hiking buddies and do more hiking. That is another him-problem, which also needs to take into account the fact that *any* long-distance hiking, biking, etc. he’s been able to do since your child was born has been facilitated by you being available to watch your child (i.e. Not Hiking).

Whenever dads have energy to work out or do other fun things and moms do not, there’s a simple, obvious solution to that. If he wants you to start an exercise routine so bad, where’s the part where he volunteers to take on the childcare duties or allocate the necessary funds for a sitter that would open up enough leisure time to make that not just possible for you, but pleasurable for you? Meaning, you get enough time to hit the yoga studio or dance class four times a week if you want to *and* catch up with friends & family *and* do other leisure activities you enjoy *and* get enough rest and time to chill out, not just that you replace all of your current free time activities with assigned workouts. He says he wants to work on the marriage, but all he’s done so far is assign you work.

There were much better ways to have these conversations. “I appreciate how you always make time for me to go hiking and biking, can we switch it up so that you can get some workouts in too?” “I really miss our sex life, can we sit down and figure out some ways to reconnect, and is there anything I can do to make carving out the time and space for that easier on you?” “If I can find a counselor, do you think we could benefit from having some outside guidance and perspective?” “If we can get the grandparents to watch Kiddo for a few days, do you want to go to this vacation spot with me? They have a lot of hiking and biking trails, but they also have yoga/pilates/dance stuff, a lake with swimming, and a great spa and massage package.” “You don’t have to do anything, just say yes and get the days off from work, I’ll plan the rest.”

You say you’re “worried that you won’t be able to meet your husband’s standards even if you tried.”  You’re correct to worry! If he’s making your post-childbirth, post-surgery body into a load-bearing repository for all of his anxieties about marriage, sex, aging, parenting, etc. you won’t ever be able to meet his standards, because they will change to fit whatever his anxiety decides should be all your body’s fault this time. When he says “…his expectation in a partner is that they be of above-average health and activity, and he’s not willing to reconsider that…” that doesn’t sound like a person who is planning to grow old together. What if you got diagnosed with a serious illness? Is he telling you that he would not stick around?

Where do you go from here? If I could wave a magic wand and send you out of town for a week with your best girlfriend so you could think things over while he does all the parenting and household stuff, I would. Maybe there’s a yoga retreat or something you could sign up for. If he truly would leave you unless you become a dedicated athlete to his exacting standards, then maybe he needs a chance to miss you for a while and make some decisions, too.

Possible discussion points: “You say you wouldn’t have married me if you’d known that this is how I would be four years in, and I guess you have a right to that opinion. If I had known you felt this way, I would have thought twice about planning to grow old with you, and I definitely would have re-considered giving birth to your child. But here we all are.”

“If you want to find a couple’s counselor for us, I’d be willing to go with you, and if you want to talk to someone on your own that might also be a good idea. I’d love to have more free time to even contemplate working out, so let’s pull out the calendar and see how we can re-balance the parenting workload to make that possible.”

“But let me be absolutely clear: I am satisfied with my body and state of health given the events of the past few years and my current time commitments. And I have zero intention of changing myself into someone who enjoys the same intensity and frequency of workouts that you do. If that’s a deal breaker for you, and you want to be married to a totally different person, then tell me sooner rather than later. I’m going to get away for a few days to give us both a little space to think.”

By negging you this way, he thinks he’s setting up a situation that incentivizes you to try to win him over/ back and prove how much you love him, and it hasn’t occurred to him that he shit the bed so hard and thoroughly here that you won’t let him near you until he can convince you that he’s worth trusting. I hope he rises to the occasion, but if he doesn’t, probably better that you find out now.

Content Note: Today’s letter contains mentions of self-harm (past, non-graphic) and advice about what to do if a partner threatens self-harm during a breakup.

Content Recommendation: Remember my friend Lenée aka dopegirlfresh, who answered letters when I was out with Guillaume? She’s running an online writing workshop geared to processing and grieving around breakups on June 12. Event link is here, fee is a pay-what-you-can donation. 

Dear Captain Awkward,

I have been together with my boyfriend for 9 years. We currently live together in my apartment. I am doing my PhD while working 2 jobs. He is trying to get a new qualification because he didn’t like his previous job, but has been unemployed for about an year. For this time he is really not focusing much on his studies, but rather watching tv and wasting his time. He feels insecure to start applying to new jobs, but he is not doing much to change that.

I went on a trip for a few weeks in Asia away from home and while being there he was fighting with me a lot. He told me that he doesn’t agree with me going on trips, he doesn’t like my job etc. Later, he apologized. I have talked to him and told him that I feel unhappy in the way our relationship is because he tends to be controlling. Through long conversations he has actually agreed to change his behavior, but so far these are only words and I don’t really know how he will act in the future. Moreover, 5 years ago he cheated on me and I feel like for these years I have been in a vicious circle trying to get over it then getting depressed because of it and so on. I am not sure if I am not using this point to rationalize my decision that I need to break up with him.

During my trip I realized that I feel unhappy in our relationship and that I probably need to end it. However, I really love him and care about him. Except the things I described above, he is a really nice guy that I deeply care about, and I just can’t imagine sitting in front of him, looking him in the eyes and saying that we need to break up after almost 10 years.

The truth is that if I knew he will be ok after that I would not be in so much trouble making the decision to do it. He has had a really hard childhood, addiction problems, suicide attempts as a teenager and so on. He is not in a good relationship with his family. He doesn’t have many friends. He doesn’t have a job or money. He doesn’t have an education. He doesn’t have anywhere to live. And he really loves me and thinks that I am the only one in his life that cares about him. I know that this all sounds way too familiar and is a quite toxic situation to be in, but I really do care about him and I want him to be ok. I have another house that I can move to, so I have no problem if he stays in my apartment for a while. What I worry about is how this all will affect him and how I should tell him. My thinking now is to start with the fact that I don’t trust him because of the cheating and that you can’t really build a family on broken trust and the second point I want to make is that my professional aspirations, even though he promises me support every time, are not really supported by him. If we continue like this will make him miserable in the future and will make ME miserable.

My question is if I should wait more so he can at least find a job and feel better about himself, or risk doing it now, taking in mind that he can get depressed, suicidal, not finish his education and not find a job. I know that I should not feel responsible for all this because I am not his mom, but for so long I have cared about him and tried to help him, that my decision now feels egoistic.

The truth is that I just want to feel like a woman. I want to feel support. I don’t want to tiptoe around how I tell my partner something so he doesn’t get mad. I don’t want to be the dominant one in the relationship when it comes to choosing where we go, what we do, the money we spend (which is all my money), the trips we go to, but also the submissive one when it comes to different things I choose not to do just so we don’t get into a fight because of his controlling behavior. In this relationship I feel like a mom, that needs to get permission from her child on what to do. I am not entirely blaming him about this situation, as we are together since we were teenagers and for this whole time I have tolerated this behavior and made him think that I am completely ok with it. Maybe if I had put some boundaries early on now the situation would’ve been quite different. But by now I am really really exhausted and I don’t think that I can continue being a mom training him how to treat me after almost a decade together, even though I see that he is willing to accept what I want for the sake of staying with me.

I would be very grateful for some advice on this situation and thank you for everything you do!

Best,
D

Hi D,

It sounds like you’ve decided that this relationship needs to end, the question is about how and when to end it and how to balance multiple competing priorities:

1) You want to be done with the relationship. That’s something you get to decide. It does not have to be a mutual decision.

2) You want him to be okay with the decision, but that’s not something you can control. Your reasons for why you want to break up are all valid, but they won’t make a convincing case for him. And if he doesn’t want you to leave him at all, how you leave him will just be part of the story of how he feels sad and angry, so you might as well do it in a way that works best for you. Don’t want to tell him face to face? Do it with a phone call or a letter. He’ll be like “I can’t believe you are ending a ten-year relationship with a phone call!” He’ll be like that no matter how you do it.

3) You want him to be okay, in general, given past struggles and current lack of employment. This is also not within your control.When you break up with someone, you don’t have solve the relationship problems and you don’t have to solve their problems anymore. It sounds like he could use a good therapist, with set office hours and professional ethics, not a 24-7 cheerleader, job-haver, and chore-doer. He is free to find one! You cannot be one for him.

4) You want accountability around the way he’s treated you in the past, some acknowledgement of the work you’ve done to carry him and be there for him.

If you could have only one of these options, which one would you choose? I vote for the first one, and I vote for sooner rather than later. How he feels and how he behaves are out of your control, and if you wait for accountability you’ll be waiting a long time. Speaking of which, you ask: My question is if I should wait more so he can at least find a job and feel better about himself, or risk doing it now…”

How long are you willing to wait? Another six months? Another year? Another nine years? Maybe you just need a third and fourth job on top of school to make up for his zero amount of jobs?

Consider that if  he is unemployed and unhappy with you in his life, the deciding factor of whether he remains unemployed and unhappy is not you. You being around to support him emotionally and financially so far is an arrangement that’s certainly to his advantage, but if he can’t even be the minimum amount of loving and kind to you in order to maintain that support, then oh well, that’s his choice! Once you leave, he will either get his shit together or he won’t. If he doesn’t, it’s not your fault, and you staying would not have made it happen. The evidence for that is whatever he’s doing now that he has you to lean on. If he blames everything on you, that’s his choice, but it doesn’t make it your fault.

I’m not going to lie to you. Breaking up with a controlling person is difficult and can be dangerous, and after you leave, things might get *very* ugly. He might well spiral back into bad behaviors. He might do everything in his power to manipulate you and get you to feel bad for him enough to come back, and that could include threats of self-harm. One thing you could do before you break up is make a safety plan where one of the elements is figuring out what you would do in case of suicide threats. If he goes there, it is not your fault. There is no mental illness where the cure is the eternal compliance of another human being. Going back to the relationship is not an option, so what support resources could you call in? Of his few friends, who might be willing to check on him? What mental health and crisis resources are available where you live?

 Here is what the beginnings of a safe exit might look for for you. It’s great that you have alternative housing available, that’s often the hardest piece of the puzzle. This is non-comprehensive and needs to be tailored to your circumstances, which you know and I do not, so it’s just a template.

-Given your worries about the possibility of threats about self-harm, I think your best course is to prepare as much as possible to be out of there without alerting him that you’re going until you’re ready to go. I know you want to ease the way as much as possible for him and not spring anything on him, but I also think that as soon as you raise the possibility of leaving things are going to get worse between you. Much worse. Preparing quietly is also a way of preparing yourself to follow through on this decision and getting in the habit of putting your own needs first. You may want to talk to a domestic violence organization where you live and get their take on things.

-As unobtrusively as you can, remove your important documents and anything truly irreplaceable out of the shared apartment and into the other house where you said you could stay. Plan short getaways to that other dwelling if you can, so you heading out with a backpack or suitcase isn’t strange. “I want to visit family for a few days!” “I want to give myself a little writer’s retreat to just work!” Keep the tone light and fun, like, “Enjoy having the place to yourself!”

-Do a general safety audit of your online presence. Clear your browser history, use private browsing for anything related to leaving him. Change passwords to your phone, email, social media, and financial accounts. Back up your PhD research and other important writing to an external hard drive and the cloud. If you share a bank account, make sure you have your own separate accounts that are not linked to the shared one that he cannot access. Use the shared account for household expenses only.

-Decide on a time limit for how long he can remain rent-free in your shared apartment after the breakup.  Is he on the lease jointly with you, or is it just you? Are you willing to give up the apartment altogether and find a new one if he’ll take over the lease, or do you need him out by a certain time? You may want to contact a local legal aid organization that deals with landlord-tenant issues to make sure you’re doing everything legally. Do not promise him he can stay as long as he needs, put a deadline on it. “I’ve paid the rent for three months to give you time to find a new place, after that you’ll need to either take over the whole lease or move out.” Sometimes people put aside money as a cash-for-keys sweetener, like, if he clears out at the end of three months with no trouble, you will give him some $ toward a new place to get him on his feet, but if he doesn’t, you can use that money to formally evict him or get a new place of your own. (Do not tell him about this money or he will immediately demand you give it to him).

-When you break the news that you’re breaking up, if you don’t want to use phone or email and insist on doing it in person, do it in a public place that isn’t your apartment. Plan to be out of your apartment that same day, and recruit friends to be on standby and come at a specific time. They can pick you up, help you pack up stuff you’re taking from the apartment, and be a buffer so you’re not alone with him after you break the news. If you can stay with someone for a few days, so much the  better.

-I know you are very worried about what to tell him, but the reasons why you’re leaving are less important than the fact that you are leaving. The more reasons you give him, the more reasons he will use to argue that you should stay and work it out. He cheated, but you forgave him, so why leave now? Are you sure you’re not the cheater? He knew there was someone else! He’s not working, but he will be soon, so why not stick around and support him on the home stretch? Is money more important than him? But you’re his only person! Etc. All the reasons you said in your letter that make you worried about him, he’ll use them against you. Any criticisms will lead to more empty promises to change. You already know how that turns out.

The important information is the fact that you are leaving. You are telling him about a decision you’ve made, not inviting him to a negotiation about fixing the relationship. “I am so sorry, but the relationship is not working for me anymore, and I’m ending things as of today. I’m going to stay elsewhere for a while to give you space and a chance to get on your feet, you’ll need to either take over the lease or move out by [deadline].” If you can and want to, give him a small amount of money for necessities and food for the next few weeks. Push any other logistical questions for later. “But what will I do about X?” “I don’t know. We’ll have to figure that out later.” It’s understandable that he’d be concerned about losing housing security and the love of his life (so far), so he’s not a bad person for asking about that stuff. The message is: Don’t panic, you won’t be homeless tomorrow, I am not trying to make you suffer, but none of this changes the fact that we are breaking up.

If you give reasons at all, try: “I realized I’m just not happy anymore.” “The relationship is not working for me.” “My career plans are taking my life in a very different direction from what you and I first planned on, and my priorities and feelings have changed.” But what about all the promises and plans you made? “I’m so sorry, but I’ve changed my mind.” “I will always care about you, but I don’t want to be a couple anymore.” He will hate this, but there is little he can argue with in the moment.

If you must mention the cheating, do it like this: “I know the cheating incident was years ago, and I tried my hardest to get over it, but the truth is I never really did. I need to be with someone I can trust, and you need to be with someone who won’t hold a grudge against you like this, so I’m ending it here before we spend another five years like the last five.”  If he tries to apologize or defend himself, stay firm. “I appreciate the apology, just like the other apologies, but it doesn’t change my decision.” “How much we love each other doesn’t change the fact that I’m not happy in the day to day. I’m unhappy and I want to leave, so I’m leaving. Friends X and Y are going to be here in a few minutes to collect me and some stuff, and then I’ll be staying elsewhere until you’ve had a chance to figure out your next steps. We can sort everything out later.” 

Having friends on standby to pick you up will get you out of this conversation before it becomes a nine-hour crying session where you agree to take him back. You need to be away from him, he needs time to process what you told him, so resist the temptation to cling or let him cling.

-Brace yourself for an extinction burst, which happens when you leave someone or set a boundary and they immediately escalate all the behavior that made the boundary necessary. You might need to filter or block his phone and lock down your social media so he can’t find you. You may need to tell his closest friends what’s up so that they can be there for him (but also make it clear that you will not be present or on call to help him).

-Friendship after love is a maybe thing, at best. Maybe you’ll be friends someday. If he doesn’t make threats. If he leaves the apartment in at timely manner. If he behaves like a friend. If you need to promise him that you’ll be friends to get out of the conversation, you’re not a bad person if you decide later that you’d rather not.

Ending an important relationship is hard even when it’s the right thing to do, and that’s as true for the break-up-er as it is for the break-up-ee. You’re doing a very hard thing, and his controlling ways are making it harder for you. I’m sorry. I hope he will go quietly and gracefully, but if he doesn’t, that’s not because you broke up with him wrong. And if he doesn’t land on his feet right away, it’s not because you failed him. If you end up grieving the good parts, it doesn’t mean that leaving was wrong. You know what you need to do, and I wish you safety and luck and all the support from your friends and family while you do it.

Dear Captain Awkward,

So there’s this woman, Amy (not her real name) I used to work with as a volunteer at a convention several years ago. I’d worked at the convention for over 15 years before I got assigned to her section. 

There were some awkward moments between us, but I acted friendly and said “sure!” whenever she’d say we should get coffee sometime or whatever, but I didn’t mean it and assumed she didn’t either. 

But apparently she did mean it, and she kept in touch after the convention, and we actually did get together a few times, and became friends. Not super close friends, but we’d meet up for coffee, share memes over Facebook, stuff like that.

Our area of the convention would start setting up a couple of days before the convention actually got started, but not everyone would be available. It was never a big deal because everyone always ended up working more than the required hours anyway. 

One year, I ended up being one of the people not available to work early. I didn’t have enough paid time off left at work, and I couldn’t afford to take it unpaid. I told Amy months ahead of time, and she said it was no problem. I still did lots of data entry throughout the year leading up to the convention, which did not even count towards our total hours worked. 

Then the week before the convention, I got a message from Amy’s supervisor saying he was going through the schedule and noticed I wasn’t signed up for the Wednesday set-up. I said I had already cleared it with Amy and I was still going to be there Thursday after work (convention didn’t start until Friday) and he said Amy was sick so he was handling things, and if I couldn’t work Wednesday they would have to reassign me. I told him again, Amy said it wasn’t a problem months ago, why was it a problem now? He said it was always a problem, and he didn’t believe me that she said it was okay. He was actually kind of snarky about it, saying “You’ve worked for us for how many years? And it only just now occurs to you that we’re up and running on Wednesday?” 

I tried texting Amy, but she wouldn’t respond. So I messaged him back and said don’t bother reassigning me, I quit. I was sad and angry about it, that all the years I worked way more hours than required meant nothing because one year I could only be available one day early, not two. 

But I was really upset that Amy didn’t have my back. I get that she was sick, but I had this weird feeling that she didn’t actually want me working with her and she was letting her supervisor do the dirty work of getting rid of me. Everyone else working in our section were friends of hers from years back, and even though they were all nice, I never felt completely included in all their inside jokes and things. 

Plus, she never apologized or explained or anything afterward, she just kept acting like nothing had happened. When Facebook would post “memories to look back on” and pictures of us would come up, she’d tag me and heart them and say “look how cute we were!” and things like that, or she’d randomly message me.

The last time she asked to hang out, I said that I still felt uncomfortable about the way things went down the last time we were on staff together, and could we talk about it? She said she wasn’t working in that section anymore, that it became too toxic, she didn’t like to talk about or think about that time in her life, and she just wanted to put it all behind her and move on. So I tried to let it go and just be casual friends like we used to, but it never stopped bothering me and I eventually just stopped responding to her. 

But every year when it’s convention time, and tons of my friends are posting about it, it all comes back to me and I’m still mad about it. At this point I haven’t talked to Amy in years, though she still randomly tags me in stuff, but I really want to just send her a message explaining how I feel. I feel like I can’t really let it go until I’ve had my say. She could chose to delete it and not even read it, or not respond, or read it and apologize, or read it and get defensive and explain how she doesn’t think any of it is her fault, I don’t know and I don’t really care. I just want to straight up tell her that I felt like she betrayed me. 

I feel like this would be a big relief, just to tell her, and I don’t have any expectations of anything back from her, I just want to get it out. But on the other hand it seems silly that I still even care about something that happened so long ago, and I should be able to let it go. But every time I think I’m over it, something will pop up to remind me and I’ll just get mad all over again. Do you think I should send her the message?

Here’s what I think you should do:

1. Compose the “Amy, fuck off” letter of your dreams. Get the last word. Get all of the words. Wail at the injustice of the universe.

2. Print it out.

3. Find a fire-safe vessel, an outdoor location, and some matches.

4. Ritually burn the letter.

5. Extinguish the fire safely.

6. Cover or dispose of the ashes responsibly. If smearing some on your face would make you feel badass and complete the ritual for you, go for it.

7. Find Amy’s social media profile(s), starting with any where the two of you are mutuals.

8. Locate the “block” button.

9. Click it.

10. Other people’s feeds got you down? Hide them for now.

11. Pull up Amy’s contact in your phone.

12. Repeat the blocking process.

13. Congrats! Now you can devote your energy to figuring out what all these feelings are really about and leave Amy out of it.

Do you miss volunteering at the convention? Find something similar to volunteer at. I’d say go back to this event and see if they have any openings for next year, because I doubt that one bad interaction with one jerk after 15+ years of service put you on some blacklist, but it sounds like you still have way too many feelings for that to be a good idea. That said, what’s stopping you from buying the ticket to the next one and going for just the fun parts? Geek out about something you love, catch up with the people you actually like minus the unpaid labor, and see how you feel. If you don’t have a good time for whatever reason, you don’t have to ever go back, but at least you’ll be leaving on your own terms.

Are you feeling a little lonely and disconnected in general? COVID pretty much wiped out casual, situational, location-based and event-based friendships where there were people you didn’t have to be close with in order to enjoy their company now and then. Maybe it’s time you joined something new.

Is this grievance against Amy occupying you to a degree that it’s getting in the way of enjoying your life? Is it reminding you of other betrayals or patterns in your life? Therapy isn’t for every problem, but this is one of the things it tends to be very good at.

Is there a friend or family member in your life who you trust to have your back, someone who is always glad to hear from you? When was the last time you reached out to them or planned a fun get-together?

If you’re still filled with unexpressed frustration after all that, can you at least channel it where it might do some good? Pester your elected officials. Clean the grout in your shower. Make some art about it. Spite is motivating!

Do you need to delete Facebook? What is it doing for you besides stressing you out so it can harvest your data and sell you racism and herbal remedies?

Let me be frank: Blaming the fact that you rage-quit a volunteer gig that you’d been doing for 15+ years on some imagined “betrayal” by someone you were on occasional meme-swap terms is not exactly giving “reliable narrator”* energy.

[*To be clear, I don’t think you are misrepresenting the facts, at all! Your account is most thorough. I think that they add up to something different than you think they do.]

From the start, everything you say about Amy assumes she is duplicitous and insincere. You didn’t really like her at first, but you acted friendly and assumed she was fake-liking you back. You grudgingly entered a casual friendship. During her time as a volunteer, Amy formed some close ties within the con community, and those ties were not 1:1 transitive to you, and somehow you translated that to her trying to prevent you from forming ties of your own. I don’t see how that’s possible since you had 15+ years to cultivate your own posse of con buds and in-jokes before you ever met Amy, but okay. You were friendly but neither of you were in the other person’s inner circle. That is…fine?

When Amy got sick and the scheduling mix-up happened, would it have been nice if she’d texted you back or got in touch with the volunteer supervisor to clear things up for you? Sure, but it’s not her fault that the replacement supervisor was a jerk to you, and it’s not certain Amy could have done anything about it at the time even if she had responded. “She kept acting like nothing had happened.” Because for her, nothing much had. Once Amy called out sick and handed off her tasks, anything and everything to do with that year’s convention was officially off her plate. If she was also having a bad experience with the organizers, putting her phone on mute for the whole week and going back to sleep makes total sense. And, you’re gonna hate this, because he does sound mean, but if Amy’s back-up person refused to bother Amy while she was out sick on behalf of a volunteer, that was 100% the right call.

You bailed on that year’s con, which was not totally unreasonable, given how rude the dude was to you. Then you bailed on the whole thing forever, which is certainly your prerogative. But then you made all of it Amy’s fault. You describe every part of it like a conspiracy Amy cooked up from her sickbed specifically to ice you out. That is soooooo much work, especially since if she wanted you out, she had a whole year to say “I’ve got all the help I need this year, want me to put you in touch with another team?” and then attend the thing she meticulously planned. This does not add up to “betrayal.” This adds up to you projecting. A lot.

“Once you quit, I get the sense that you wanted Amy to seek you out, find out if you were okay, beg you to come back, and do something to repair the situation. She didn’t. Sorry. She was not The Convention You Had Toiled At For Lo These Fifteen Years, she was one fellow volunteer who wasn’t even there that day. What could she say except, “sorry that happened?” Sometimes when you leave something, people don’t chase after you. They assume you have your reasons, or, they have their own stuff going on and simply aren’t thinking about you as much as you’re thinking about them, or, all of the above..

When you finally had a chance to clear the air, Amy was clear: She was not willing to revisit the topic of the con that wasn’t, but she was willing to resume a casual, friendly connection and hold onto the good memories of hanging out. And since then she has remained….:checks notes:….consistently pleasant. She doesn’t hate your guts, but she also does not want to discuss something painful for her with someone who clearly will not let it go. You want closure? There it is. You get to close the door from your side, too, and it sounds like you have. (I eventually just stopped responding to her.” “At this point I haven’t talked to Amy in years.”)  I repeat: Sometimes when you leave something, people don’t chase after you.They assume you have your reasons, or, they have their own stuff going on and simply aren’t thinking about you as much as you’re thinking about them, or, all of the above..

You’ve already all but ended this, so why the demand for acknowledgement and justice now? You’re asking me if I think it could be healing in some way if you rage-dump on a former casual friend from a former volunteer gig you haven’t actually talked to in years, even though you swear up and down that you don’t expect any kind of response from her. I can’t go for that. No can do. Whatever this is, it’s a conflict between you and yourself, and poor Amy’s just playing the part of neighbor with the wonky eye from The Telltale Heart that you can’t stop thinking about. She is not harming you. She does not owe you anything. Leave her alone.

“….I feel like this would be a big relief, just to tell her, and I don’t have any expectations of anything back from her…”

Bullshit. Once you hit send, you’d be hitting refresh until your hand lost feeling, and her blocking you immediately would be the best possible outcome for everyone. But if you are telling the truth about not needing any response from Amy to put this to rest, then telling us about it in your letter and sending the rest up in smoke will have the same effect. You’ll get the last word, you’ll get to set it on fire, and then you’ll be free.