Dear Captain,

I am in a tough place with a long time close friend. My partner and I are currently roommates with this friend. We have been all living together for a little over a year in a shared apartment (everyone’s name is on the lease).

Friend is a wonderful, kind, smart person, but he’s been in a bad spot for the past 4 years and seems to constantly be in a very slow decline. We are all in our early to mid 30’s college educated professionals, but roommate has not worked consistently in years and nearly at all in 3. He’s been fired from multiple positions in a row. He has not ever had a relationship though he claims to want one. He is not in school, volunteering, or otherwise doing anything to move forward in his life. He’s clearly struggling, but while he’s openly discussed that he’s had issues with anxiety and depression, and is on medication/sees someone about this, he otherwise attempts to act like everything is completely fine. He spends large amounts of money he doesn’t have on his hobbies, hangs around the house constantly in his pjs, sleeps very late/stays up all night, and really only goes out if its to do something “fun” or if it’s related to his hobby, and is often not conscientious to the household as a whole.

Other notes on our and roommates situation

– He does pay his portion of rent. See next point for more on that

– He is not in a position to not work. He is being given cash by family members to float expenses but there is also large amounts of debt on multiple credit cards. His family is not able to do this indefinitely and it’s clear that his finances are a house of cards that is going to collapse.

– Partner and I do not want to live with roommate after our lease is up. We have a few more months on the lease, and for us all to find housing we need to inform him now. We do not plan to kick him out. Current plan is to offer to either turn the apartment over to him and move out, or take over the lease if he’d like to move. However I doubt he will get it together enough to make a plan to move (see above stagnation), and there is a high likelihood landlord would not allow him to remain in the apartment without us (see lack of income), so us moving “kicks him out” by default

– His alternative free housing option would be with a family member. This is roommate’s last choice option and he would hate it. It is not unsafe or abusive, but it would not be what he wants

– He does not have a drug or alcohol problem ( I am 99.9% sure of this)

– We knew he was having issues when we got a place together. At the time we thought it was more situational and less due to his actions/ lack of action, and that living with people who cared about him and were also productive adults would be helpful to roommate. My partner and I both agree now moving in together was a bad call on our parts

– We live in an area where finding employment in things like retail/ serving jobs/ temping etc is not difficult. He seems to think this type of hourly work is beneath him.

– It’s clear he views himself as a part of me and my partner’s family unit and seems to think he will remain as part of our household indefinitely.

At this point myself, my partner and all our mutual friends are extremely concerned about him. It’s become clear that his situation is a slow moving disaster but that eventually he’s going to hit some type of wall and not be able to continue on pretending everything is fine. Conversations to try to help him or make him see reality have been unsuccessful. Having a frank conversation with him is like nailing jello to the wall.

My question is, how do I explain to him that we are not going to be living with him on the next lease cycle without destroying our friendship or setting in motion an emotional collapse from him, while also making it clear he needs to take this seriously and make plans on how he’s going to house himself going forward. I’m worried about having to spend the next several months with an angry and seriously depressed roommate or alternatively him in a panic come the end of the lease when he’s done nothing to prepare. I do feel like I have some responsibility to preserve his mental health and our friendship in all this.


Failure To Launch’s Roommate

Read More


I’m hoping you can help me with some coping mechanisms for jealousy which will help me feel less like the shittiest friend in the universe. 

Long story short, a friend got a job I wanted, and I’ve spent months failing to not let it affect our friendship. The whole story is long but the important details are these:

She got an early start in the “big leagues” of our industry because of connections I didn’t have, beating me out for jobs before I even knew her.

A mutual friend promised me I’d be his first call on a job I really wanted, but then hired her.

I had a hard autumn, and overwork combined with personal insecurity culminated in me, in tears, while she tried to console me over the job she was (very rightly!) excited to start the next day.

She’s just gotten the reiteration of that job I really wanted. I’m still angling to get them to hire me too, at a lower title than hers.

Last fall I tried really hard to be supportive and excited for her and mostly failed. I’m afraid to spend the rest of her time in our city (she plans on moving… eventually) watching her get jobs I am equally qualified for because her resume is better. I also don’t want to look forward to the day she moves, just because it means I won’t have to compete with her for work anymore. I don’t want to feel like a terrible friend anymore because I can’t be happy for her, and I absolutely don’t want to force her to console me on big happy occasions.

I think her fiance dislikes me and I worry she confides in him that she feels uncomfortable in our friendship, or that she thinks I’m an incompetent artist. I will never actually know without damaging the friendship by pushing the issue, but it bothers me anyway.

I have read your “focus on yourself and what you like” advice, and the “back off and gently let reconnection happen” advice and that has been helping, but I’m worried that watching her have a job I wanted will disintegrate our friendship, or worse, if she doesn’t, or isn’t able to hire me. I need a way to restructure what’s happening in my head so I’m not feeling overwhelmingly betrayed by this friend who hired her, and jealous of her all the time.

Read More

Dear Captain Awkward and friends,

Due to frequent moves both by me and by many of them, the seven or so people I consider my closest friends are scattered across three countries on opposite sides of the globe. (And most of them don’t know each other.) Nevertheless, I keep in frequent contact with them – we communicate at least once a week, often more. I’ve known them all for years (several of them for decades), they’re all very important to me, and they’ve been there for me in tough times, so I don’t think this problem indicates a major break in our friendships or anything like that, but. Yesterday was my birthday, and not one of them remembered it.

My birthday isn’t public on Facebook because I never liked the hollow “hbd” posts from people who I don’t really interact with. So the lack of a Facebook reminder is almost certainly a factor here. But I know that these seven friends know when my birthday is, and all of them have sent me birthday messages unprompted in the past. I didn’t even expect messages from all of them this year – it’s just that not receiving even ONE hurt a lot more than I thought it would. Especially because it’s not a secret that my birthday is important to me, moreso now that I have stopped celebrating most major holidays. Maybe it makes sense that more of my friends wished me a merry holiday-they-know-I-don’t-celebrate-anymore than wished me a happy birthday, but it still sucks.

And I don’t think I’m being a hypocrite here! I try hard to remember my friends’ birthdays, whether or not they have them on Facebook, and I make sure to send them birthday greetings. Which was all I wanted in return. One birthday text from a friend and I wouldn’t be writing to you!

Anyway. Any thoughts on how I should handle this? Do I bring it up with them? Do I admit how much it hurt? Should I obnoxiously remind them next year? Or should I focus on the nice messages my family sends me and the kind words from the friends I’m making in my current location, and try not to worry about my friends elsewhere? Do I just need to accept that if I don’t let Facebook announce my birthday, no one will remember it?

Thank you,
Birthday Girl

Read More

Dear Captain Awkward,

Four years ago, the first fling I had after I left my ex was with a guy at a large multi-day costume event in a far-off state. He came on really strong (in character) and as we have friends in common, I knew he was engaged and asked him about this. He eventually explained to me that he had permission from the fiancée to fool around above the waist, and as this is pretty common in our circles, I liked him, and I was about to go back halfway across the country, I figured what was the harm to have a little fun?

So we made out a little, and kept writing to each other flirtatiously after I went home. I wanted to come back for the final weekend of the event, and he offered to put me up at their home. I had been pressing him to tell her about us, and he said he was waiting for the right time, finally saying we’d all go out when I got there and he’d tell her then.

Long story short, “circumstances” intervened so that he never told her, she found out and chewed me out (with him standing there not stopping her), I had to find another place to stay in the middle of the weekend, and I was livid with him for ruining two potential friendships (with him and her) and cut off contact with him.

Months later she wrote me apologizing for yelling at me, said they had both worked everything out, and asked if I would consider being friends with him. I said yes, as long as he agreed never to flirt with me again.

Now he is a bit of an unusual guy. The characters he plays in these costumed events tend to be overly chivalrous and attentive to women (opening doors, pulling out chairs, getting the check) and that tends to carry over in his real life (he also has a lot of hobbies related to historical re-creation and crafts, and tends to like vintage things generally.) So what I might read as creepy boundary-pushing attention, due to the massive breach of trust he committed, others have just told me they see it as flirting/overpoliteness/old-fashioned aesthetic, and don’t really have a problem with it, just see it as harmless.

He tends to fall back on flirting-as-a-social-lubricant, because that is his comfort zone. He flirted with me a couple of times when we bumped into each other at a costume event after we had reconciled, but we also had drinks recently, out of costume, where he behaved himself.

As a modern woman, I don’t like pro forma chivalry in my normal life, but I can go with the flow of being “treated like a lady” at historical events if I know it’s all pretend. But with him, it rankles because I’m not convinced it’s all an act.

Recently I went again to the same event and spent a little time talking with him in character (during which he fawned a lot, flirted, and then apologized for flirting when I seemed to be bothered by it) and afterward, we went out with friends, during which he sat next to me, suggested we order stuff to share, and seemed to find excuses to brush up against me, which made me super leery. Usually, when he oversteps, I call him on it, but I didn’t do it during dinner because I didn’t want to have the big awkward conversation with friends there, and the breaches were slight enough that it felt like it wasn’t worth it to correct him.

So, since for the last few years he’d done little to restore my respect for him, or given me any consistent reason to trust him or his promise not to flirt, I made up my mind that I was done seeking out his company, although I’m okay with an occasional brief friendly interaction, and as we don’t run into each other very often, that’s not really hard to accomplish.

But he wrote me a couple weeks after that saying he’d had a dream about me being repulsed by him and was worried it was his subconscious telling him he had overstepped, and wanted to check if everything was ok between me and us. He said he admired my charm and talent and also liked me a lot, and that it was hard sometimes not to show it.

I’m not sure how to respond, or if I should. I’m going to be around his neck of the woods a lot next year and I’m worried about possible future interactions, especially since I like going to costume events in the area and we also share a group of friends.

A pretty timely problem to have, considering open and vocal disdain for creepiness is currently in the zeitgeist.

What do you think?

Read More

Dear Captain,

I write fiction, mostly fantasy. I admit I can be humorless about it. My friend “Shawn” writes fiction of similar genre. We used to talk about writing and about our ideas a lot, but less so since I got a day job.

Shawn starts projects all the time and most of them never come to a full rough draft, so I know not to get too invested in any particular setting or character concept they tell me about. (OTOH, due to my more limited free time for writing, I’ve just got the one novel I’ve been revising for a few years now.) My issue is that Shawn keeps telling me about all of these ideas, with no context. They’ll text me out of the blue, “I’ve decided that Character X and Character Y are going to date” or “I’m setting my next story in a fantasy version of Tibet” and I have no idea how to react anymore. I’d be happy to read any completed stories that came from these ideas. I’ve read their one completed manuscript and, hell, I’d be happy to hear random thoughts about that setting or those characters, who I already care about. But what on earth do I say to “My new character is a dragon and her favorite soda is Ramune,” especially when I know I’ll never hear about this dragon again?

I wouldn’t mind if I got to talk about my own writing in turn, but they don’t seem interested anymore. They asked to read my manuscript once, and (a year later) have finally stopped pretending they’ll ever get around to it. Recently they asked me a question about my protagonists, and I got excited at this sign that we could resume shop talk like we used to. But after I answered, they just said “Nice” and used it as a springboard to brag about their own great characterization, in the context of another story they had just thought up. I kinda feel like my time and effort are being disrespected here.

Am I being snooty about different approaches to the creative process? Am I being too precious about my own work while judging theirs harder? If not, how can I steer these conversations back to a fun and mutual place, and not a place where I’m getting infodumped on?

A Wiki for a Fictional Multiverse that Doesn’t Yet Exist (they/them)

Read More

Dear Captain Awkward,

How is a good way to let a friend know that her mildly homophobic comments are hurtful to me before I move in with her?

My friend Ella would probably be offended if she knew her comments come across as ‘othering’ to me (I’m a bisexual woman, not yet fully out to her, and only newly out to myself). Nonetheless, the things she says make me feel I can’t be fully myself around her.

When Ella heard I’d been on a date with a woman, she grilled me about my sexuality at a point I was feeling uncertain myself and unready to talk.

Now when we go clubbing, Ella will grind up against me, pant against me and generally invade my personal space in a way I don’t like while looking at all the men near us. It makes me feel like she’s trying to ‘put on a show’ to attract men, and I don’t like being a part of it.

Ella has often said things that make me think she views sexuality as very binary – a female friend of ours was once in a three year relationship with a woman, and is now with a man. Ella immediately dismissed the previous relationship as “just experimenting”.

Ella has low self esteem and is dealing with anxiety right now, which is why she wants me to live with her. She’s a nice person and I think it could be really fun to live together, but not if these things that make me uncomfortable continue.

How can I respectfully and kindly assert what I need, Captain Awkward?

Sincerely yours,

Not in Kansas anymore

Read More

Dear Captain Awkward,

I have an awkward social situation that I’m not sure how to handle. It’s been causing me a bit of anxiety, and so I’ve been avoiding dealing with it.

Recently I have had a rash of old friends who I am no longer close with contact me, wanting to either catch up or get together. Some of them I’m happy to have a chat with and tell them about my life and hear all about what they’re up to now, but when they suggest we start hanging out again I feel stressed. The problem is that I simply don’t know how to fit these people into my life now.

For a long time I was very mentally and emotionally unhealthy, and I self medicated with drugs and alcohol a lot and was a bit of a party girl. Right now I’m the healthiest and happiest I’ve ever been, and I can look back on those years with new clarity and insight. I see now that I tended to be drawn to people who were dysfunctional because it allowed me to feel like I had my shit together, even though I really didn’t at all. I’ve done a lot of work on myself since then, and I feel like a lot of the friendships I made at that time in my life are no longer fulfilling to me. I’ve purposely distanced myself from a lot of people, not because I think they’re bad, but because I now find their company totally draining. Hanging out with them became something I did out of a sense of obligation. I felt guilty at first until I realized how much happier and calmer I was without them, and that I now had room in my life to make new friends.

There’s one old friend who won’t give up trying to contact me, who I particularly don’t want to see. We didn’t have a falling out, I just realized that I didn’t really like her anymore due to her rudeness, self centeredness, and flair for the dramatic. I was ok with it when she moved a bit further away and we lost touch for a while. I hadn’t heard from her in a couple years, and I was pretty relieved. She texted me at the start of this year saying she had moved back into town and invited me to her birthday party at a bar. I felt an immediate sense of dread. Since it had been a couple years, I pretended that I got a new number or something and didn’t reply. Maybe that was wrong or short sighted.

A few months later she found me on social media and messaged me “WHEN ARE WE HANGING OUT?!?!” which both terrified and annoyed me. I thought it was a rude way to make contact with someone she hasn’t seen or heard from in years. I felt put on the spot and uncomfortable. It made me want to get together even less. I didn’t reply and hoped she would get the hint. She didn’t.

A few weeks ago she found me on another platform and commented on one of my posts “Hey! Let’s hang out!!!”. I didn’t reply and haven’t posted on that platform since. This morning I woke up to a direct message from her saying “(my name)?!?!”

I think at this point I need to be direct because she is not getting the hint and it would be cruel of me to continue this tactic, but I really have no clue what to say. I’m not mad at her, we didn’t have a falling out and there’s not really a specific instance that made me not want to be friends anymore. I don’t want to be hurtful. I’ve been on the other side, attempting to reconnect with someone and realizing that they had no interest. It sucked but I got the hint and let them go. For me, this friendship is over.

What do I say?


Chronic Avoidance

Read More