Situation: I’m a white lesbian who’s roommates with a white straight guy who is also a friend and coworker.

Problem: He keeps talking about his penis.

You see, his penis has likes and dislikes, and its preferences have a LOT to say about western civilization and human nature. He will tell me at length he does not like overweight women or black women or “dominant” women, and he also has a lot of theories about men and masculinity and “dominance” he enjoys expounding on. You know what they are. Perhaps unsurprisingly, his (thin white “traditional”
girlfriend) dumped him because he kept sexting “BBBW” asking for “punishment.”

He’s on a business trip. When he returns, I anticipate more theorizing about the supremacy of the white male, lying about what he did to get dumped and posturing based on that, and more than a little pressure on me to be her friend and convince her to take him back. Once he accepts she won’t, he’ll foray back into dating and have MORE theories about women and men to share.

I don’t want to listen to or deal with any of that. I don’t want to have to think of things to say. I’m not interested in being friends with his ex, and I’m certainly not going to woo her back for him. I don’t want to call him out for being a sexist, racist douche or educate him on how not to be a racist, sexist douche. I hate arguments and loathe “debating.” I don’t want to therapy him through how his worldview doesn’t gel with his true sexual preferences, or deal with his embarrassment should he realize I’ve seen the texts. I don’t want to piss him off or deal with drunk tears. I want him to shhh and move along to things like bitching about work and eating wings and being snobby about beer and watching trashy tv.

I’m looking for neutral conversation-enders or ways to change the subject back to the things that made us friends to begin with. I’ve been using things like “huh” + subject change; some of the other scripts I’ve found on your website like “why would you say that” and “wow, you really said that” and “i don’t get it, explain” [+ make him
repeat himself until he’s embarrassed] do not work. Phrases like that just make him think he’s having a real conversation and I just end up hearing more. Unfortunately, “huh” + subject change isn’t going to work for this, because in this case it’s important enough to him and he’s upset enough that he’ll keep dragging the topic back around.

So far, I have a dozen variations on “get a real therapist.” I also have “be out of the apartment on the weekends” and “forget to turn my phone ringer volume up” and “be asleep when he comes home.” There are mobility and financial reasons “moving out immediately” is not on that list.


Not Cesario (she/hers)

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Hi Cap’n. 

Here is issue: My partners’ ex, and boundaries.

I have great relationships with my exes, I think it’s healthy and awesome. This is a new and different world, apparently.

My partner’s most recent ex is in our lives a LOT. There are good reasons for this that go beyond their ongoing friendship, but the upshot is that Ex has visited and stayed at our house approx. 1 week out of every month for the last four months. Ex and I get along… mostly. But we would likely not be friends in real life. She’s great in lots of ways but also incredibly different from me. To be honest I find her exhausting and sometimes horrible: a vain, high maintenance, superficial, demanding, selfish Regina George type. She calls other women “ugly”… a lot… she keeps everyone waiting for Makeup Reasons. She wants us to go to clubs and wears shoes she can’t walk in. Etc.

She also has radically different ideas about appropriateness from me: the first time I met her she walked topless past my partner, dropped trou with no warning and peed in the bathroom right next to me, etc. It’s not just her, they fall into these patterns together- he carries her purse, invites her to sleep in our bedroom (and bed!) to “be courteous to our roommate”, keeps me waiting at the house while they eat nice lunches, delays our special two day mini-break (for my birthday) for hours to do her sudden huge favors.

He knows this is shitty when I calmly (or occasionally shakingly) point it out. But he doesn’t anticipate it, and doesn’t predict the cumulative awfulness of it or why it means he should cool it on inviting her along on trips with us. He does feel terrible, and is incredibly patient and loving when I have an “I’m now an awkwardness alien who can’t fucking Person anymore” freakout. Never does annnything resembling deflection or gaslighting.

At this point I need a big, fat break from this person. And to take approximately ten thousand baths.

So tell me, how do I stop feeling like I have to constantly be the Boundaries Police, and do you think that’s even going to be possible?

(Not pictured: frequent references to their past, all their orgies and predictably boundaryless sex life. I’m all for fun group things, but I need to soberly discuss them before they happen. Again, he gets this, but has yet to demonstrate that as a practical behaviour before I find myself in a position of awful panic.)


Ps, he is otherwise a dream, best partner I’ve ever had, no question. Just, ack. This is not nothing.

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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

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Hail Captain! (And Awkwardeers)

I come to you with a question regarding boundaries and the ways to professionally enforce them. Some background: I’m a law student of a certain age (mid-30s) and a custodian to 2 cats (a black and a gray). Meaning that no matter what I wear, I’ve got some visible cat hair on all my outfits. After being a cat mom for 10 years, I’ve come to terms with it. Because honestly, my entire life (furniture, clothes, cars, to my casebooks) has some cat hair on it. And before anyone asks, yes I do try to curb the worst of it, but my cats are prodigious shedders. I can spend the minuscule bit of energy not devoted to school driving myself nuts about it, or I can just let it go and enjoy the fact my kiddos love me and want to be with me.

However, for my 22 year old cohort-mate, this is a way of life she can’t abide. This young lady feels extremely free to reach out and being removing cat hair from my person whenever she’s within arm’s reach. She does it in class, when I’m sitting beside her. She does it in casual conversation, when other people are present. I can only surmise she’s a “motherly” type, who thinks she’s helping. Or she’s got a thing about stray hairs that just makes her nuts. But Captain, as an introvert and adult woman, I don’t like it when someone who’s not the list of approved “touch me whenever you like” people touches me.

Captain, I’ve told her repeatedly to stop, that I don’t care if there’s cat hair, that I like it just fine, that maybe I want to take my babies with me all day! Her response is “It bothers me” as if that’s a valid excuse for breaching the sacred three foot bubble. Apparently she comes from a house of sisters, where this behavior is normal. Whereas I and my brothers outgrew the phase of just manhandling each other ten years ago. I want her to stop; I’ve told her to stop, but apparently what I want doesn’t much matter.

Captain, part of this program is hearing repeatedly that our professional community is very small, that we’re establishing our professional reputations, and that our behavior is being monitored. So making a scene isn’t an option I can take. I need some thoughts, or even a script on how to make a “professionally appropriate scene” to get this young woman to keep her hands to herself!

Any insights you can suggest would be appreciated,

Covered in Cat-hair

(she/her pronouns for both parties)

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Dear Captain,

I’m a woman in her mid-30’s who’s been dating a man a few years older than myself. We’ve only been together for about 6 months. Neither one of us has a very extensive dating history; he’s only dated one other woman, and I’ve only dated two other men. At first he seemed like the perfect match for me – we have the same quirky sense of humor, we share some similar interests, and we usually have a good time together. He’s also been very considerate of the fact that I’m extremely introverted and require a good deal of alone time.

I do have a major concern, however, and that is that we seem to have different ideas as to what our relationship boundaries should look like. For example, I’ve been saving up for the past two years to take a trip to Europe, and I finally have enough money and vacation time saved. I’ve been planning this trip long before I met this guy, and this is something that I’ve been looking forward to doing by myself. Also, I knew that he wouldn’t have enough money or vacation time saved up (his job gives much less vacation time then does mine). When I told him about the trip, however, he basically tried to invite himself along. When I tried to stress the fact that this was something that I had planned to do alone, he argued that we’re in a relationship now and we should be doing things like this as a couple. He went home and talked to his friends and his therapist, and apparently they told him that he shouldn’t be so upset that I want to go on this trip without him. So now he’s saying that I should go by myself, and have a great time – but he expects that we’ll talk on Skype every single day. I’m not entirely sure how open to compromise he’ll be on this – I was pretty upset about the whole thing – but I certainly don’t plan to call him every single day from across the globe.

(I had some concern about this a few months ago, when he basically invited himself over for Thanksgiving dinner when my parents were visiting. However, I wanted my parents to meet him, and everything worked out fairly smoothly, so I kept my mouth shut at the time).

I’m just having a lot of trouble with the fact that a) he tried to invite himself along in the first place, and b) the fact that now he thinks he can decide how often we’ll talk while I’m gone. I’m also aware that he’s going through a really rough time right now (he’s dealing with the recent death of one grandparent and taking care of another grandparent with Alzheimer’s, and his job situation is also not very good). So I’m trying to cut him a lot of slack. I’m also aware that I might not be communicating my expectations for our relationship as well as I could – I just never dreamed that he would react like this. I could really use some advice on how you think I should proceed from here.

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Hey Captain!

I’m a single straight cis woman.  Some time ago I joined a new hobby group, and it’s been great!  There are lots of men in the hobby group and a number of them have asked me out on dates.  This isn’t the problem – I appreciate people who take the chance to ask me out outright and I am good at turning them down politely but firmly when I’m not interested. 

My problem is with the people who clearly appear to be romantically interested in me, but instead of asking me on a date they just kind of weirdly hover around me.  For example, they might suddenly take an interest in all of my Facebook posts, even when they have nothing to do with our shared hobby.  Or they might just keep starting chats with me online.  They might also try to engineer hangouts that are very clearly stealth dates, or they might focus all of their attention on me even when there’s a whole group of us and we are all doing the hobby together.  I find this very off-putting but I don’t know how to address it.  Since nothing is explicitly being said I feel somewhat paralyzed in these situations and tend to just act friendly but also kind of evasive in hopes that they will get the hint, but this doesn’t always work.  Is there a more effective way I can deal with this?

Thank you,


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Yo, Captain!

I have a friend who I care about dearly but he keeps sending quite rude (almost downright racist) messages over a group chat I have with all of my friends, often targeted towards me and my heritage. A recent example is that he sent a photo of a map from almost 200 years ago and said “Ha, look, your country isn’t even on this map! It’s not a real country lol.” Another was when he kept trying to explain and then lecture me (quite patronizingly) about this country’s history (with inaccurate information, if I may add that) although I have family from this country and have read books about its history. I have told him that I find this rude and I have heritage from this country but I grew up in the same country he has, so I don’t understand why he can’t accept me as at least both nationalities. I used to be bullied for having “foreigner” relatives and being related to said country and his behaviour is similar to how it started out when I first was bullied (by other people, to clarify) which is making alarm bells ring. As it is on a group chat and I struggle with anxiety and confronting my friends (he knows this), then I find it difficult to call him out on his behaviour and I try to ignore the group chat, however, I feel like if I constantly ignore it every time people accept this behaviour more and it hinders my ability to communicate online to my group of friends (also, they know I get upset about it but I don’t expect them to do anything).

My solution was to block him on Facebook so he can’t directly message me and to avoid him on the group chat, which worked except he found out that I blocked his messages and keeps trying to call me out on the group chat. Other friends keep messaging me saying “why have you blocked him?” and then they post screenshots on the chat (so far I’ve replied with “what? I think my messages are just messed up at the moment”) so I’m afraid to tell them because these kinds of jokes are often made by him so that’s partly why no one goes “hey that’s not cool, friend.” I don’t want to be seen as humourless by telling everyone, because then people treat me like they’re walking on eggshells. Am I being irrational? Are they entitled to an explanation? Are there any scripts you could possibly give me?

Thank you,


I Just Want To Talk To My Friend And Not Get Upset (she/her)

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