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Dear Captain Awkward,

A couple of months ago, one of my best friends (we’ll call her Beth) and her partner (we’ll call him Dylan) broke up. Beth and Dylan had been together for six years and living together for five. They seemed to have a pretty good relationship, although Dylan dominated the apartment with his belongings, said he couldn’t marry her until he was a “real adult” (at 34, while doing nothing to move toward his definition of “adulthood”), and was generally kind of moody. Beth did most of the adult work in the relationship, including keeping a job she didn’t love in order to support them financially and doing all the emotional labor because Dylan wouldn’t go to counseling, individual or couples’.

They broke up because Dylan deleted their anniversary on Facebook. When Beth asked him about it, he confessed that he had been secretly dating a coworker and no longer loved Beth. She was blindsided, not least because she was very good at checking in on the relationship and he had essentially gaslit her into believing that everything was fine for months. Dylan moved out of their apartment and Beth actually packed his boxes for him. I did everything I could to support her and tried very hard not to set Dylan’s things on fire and to discuss my deep contempt for him with mutual friends instead of with Beth. Eventually it came out that the coworker was married and she created a lot of drama and misery for Dylan, and I thought, Great! He’s getting his and I don’t have to do anything.

Unfortunately, now that his little fantasy didn’t work out, Dylan has decided that he DOES love Beth after all, and he is insinuating himself back into her life and her apartment. She told me yesterday that they were having sex, but that he “can’t make any promises right now” and he says, “We shouldn’t be doing this” (while still managing to fuck her), which is basically the sexiest thing someone can say. Beth, heartbroken and holding out hope that he’ll come back to her and they can make it work, isn’t doing anything that I haven’t done myself, but I am furious that Dylan is taking advantage of her feelings so he can have AND eat ALL THE CAKE. But of course when I tell Beth that, I become the Bad Guy. Captain Awkward, I don’t know how to support my friend while also making it clear that there’s no fucking way this guy is getting back in our good graces, especially not with this behavior.

Thank you for your time!

Hard-Hearted Harpy Wants Friend to Be Happy (she/her pronouns)

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Dear Captain Awkward,

Here is my situation: My husband and I generally get along great. But one thing that routinely proves to be a problem is the concept of time: that is, when we should depart to get to a place before the event we have tickets for/need to be there for/whatever commences.

He’s a “shave it to the last minute” person. I am a “I need a buffer of time because everything takes longer than it should and also when we get there I might want to use the bathroom/get a drink of water/want a moment to breathe/get a good seat” person. Shaving things to the last possible minute stresses me out.

This has been the supremely boring subject of multiple conversations over the years. I tend to organize things and will say “we should leave at this time” to which he’ll ask how long it takes to get there/when it starts. Then the dickering over five or three minutes commences. And he’ll expect me to explain in detail why I have to leave earlier than he believes we should. I do understand that if we have a morning event he’ll want to be able to get in as much sleep time as possible, since he battles insomnia. That said, I don’t surprise morning events on him: he knows ahead of time.

I could passively-aggressively tack on 5-10 more minutes to his question of “how long/when do we need” to get there, but that’s lying – and he’s not a dummy. He will figure this out, and stop trusting my word. Either way, the problem does not resolve.

Nor does he propose alternatives to departure. A recent trip would take us 35 minutes to get to a city tour. I wanted 45; he said “no.” Not “how about 40” but no. This led to an over hour-long discussion that again had me reiterating that by shaving it close I am totally stressed out.

I am exhausted. I have said I could just leave earlier and he could depart when he feels the time is right, but that does defeat the purpose in going together as a couple, and he didn’t like that anyway.

A previous argument like this ended with him agreeing that if I organized the trip, he would go along with my timing for departure. That fell apart instantly with our city tour argument (see above). At the end of this most recent discussion, he asked me to explain to him every time that this leaving time is important to me and it will stress me if I don’t leave at this particular time. Why should it always be on me to justify?

I have tried to use my words. I have tried to offer suggestions. Mostly, it makes me not want to organize outings at all with him, which is also not a road that’s worth going down.

If you have scripts that I can use that I obviously have not thought of before, I’d really love to hear them. And maybe I’m the problem here – so if I just need to do more flying by the seat of my pants, do feel free to tell me. (When he chooses the outing, I generally will go when he wants to go.)

Thanks in advance,

Are You Ready Yet?

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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.)

Halp.

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 Awkward,

I’m Luke from #728. (The Solo family is fine, no worries.) I got a lot of mileage out of the suggested scripts then and I find myself in need of some completely unrelated scripts now.

I am not usually a dating-type of person. I’m not anti-dating. I’m dating agnostic, if you will. But I’m over 30 and don’t date and get a lot of “Your biological clock is ticking, dear” from *everyone* because hell is other people. Anyway, a dude I’ve known forever asked me out and we went on a handful of dates over a three-month period. I thought we were fine! Spoiler: We were not fine.

I have a dog named Crybaby. I mostly call her “Babe” or “Baby.” This has never been a problem before, because why would it? But this dude came over to pick me up for a date and went off on a four-and-a-half minute MAXIMUM VOLUME FEELINGSBOMB in the middle of my kitchen about how calling the dog “Babe” was disrespectful to him (??), calling her “Baby” was disrespectful to our future children (!!), and disrespecting him and our future children was disrespectful to his mother (?!?!). I just stood there and stared over his shoulder at the clock on the wall until he finished blowing up. Then he walked out, slammed the door, and got in his car.

I got a baseball bat, dialed 9-1 on my cell, and stood at a window with my thumb hovering over the “1” until he drove away. Apparently, I was supposed to run after him and apologize? I changed into sweats, gave Crybaby a treat, and ate a pint of ice cream for supper because that was upsetting.

The problem is, my entire family knows his entire family. My dad and his dad and his uncles all belong to the same hunting club. My sister and his cousin are besties. Our grandmothers go to the same church. I am in a book club with his mother. My options seem to be (a) quit society and move to a cave and eat worms, or (b) spend the entire holiday season explaining why I won’t return this dude’s calls *at Christmas*. I don’t want to eat worms! I want to strike a balance between “He doesn’t like my dog so he’s dead to me” and leaning into the other person’s space and saying, “He stood this close to me and SCREAMED LIKE THIS for four minutes because he doesn’t like my dog’s name.” This is so bizarre. I am at a loss. If you could suggest any kind of scripts for this clusterfudge, I would very much appreciate it.

Thank you,

Luke

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Dear Captain Awkward:

I have been in a relationship with my boyfriend for four months, though he has been a friend of mine for 12 years. He is intelligent, well-read, funny and very sweet. So what’s my problem? I feel like he is a bit of a man-child, for lack of better words. First
off. He lives with his parents still. He is 31. This is for the reason that he is in university, and his parents want him to “graduate without student debt”. They have never charged him rent. This isn’t because he needs his money to pay off school: they are
paying for his education in full as well. They make him meals, check up on him to see if he has packed a lunch for work, make his bed and clean his room. They recently bought him expensive new work boots because, not because he couldn’t afford it, but because
he doesn’t think it’s necessary to have footwear for work that isn’t falling apart.

Don’t get me wrong. His parents are the most wonderful people. But he’s 31, and will be in school another 2 years. Which means, he will be living rent-free with his parents
until school is done. He works, but only has to pay for his car and phone. He also seems emotionally immature. Everything seems to have an excuse or be my fault. He hates conflict, so whenever anything comes up that is important, he shuts down. I feel I am
always the one to initiate apologies, conflict solutions, and conversation in general. I feel like I am the one carrying the emotional workload, and constantly having to explain the “real world” to him, because he is so sheltered. I need him to step up emotionally,
and for him to learn how to continue growing as an adult while under his parents roof. I don’t know how to bring this up without upsetting his parents (he tells them everything I say) and hurting his very sensitive feelings.

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Dear Captain,

I have a colleague, “Peter”, who I’ve known for several years. We first worked together at a festival, and added each other on facebook/phone for organisational reasons, as he was the crew leader. Over time we have become friends, although I do see him as more of a colleague as he is 20 years older than me with a kid, and I’m a student. I worked with Peter again this year, and during the festival he split with his girlfriend. Naturally he was upset, and I was sympathetic – at first.

Recently, he has been pestering me on social media, and on the phone when I ignore his messages. I shouldn’t ignore him, but he frequently sends me random unsolicited updates on his life/ weirdly personal accounts of his break up, often at 2am, and I don’t know how to respond. Sometimes I will commiserate, but then he will turn on me and ask these loaded passive aggressive questions like “you really ok with this?” or “am I being obtuse”, so I have stopped responding as I don’t have the time or emotional energy to deal with him right now.

I think he is just looking for a friendly ear, but I’m struggling to deal with someone who is so emotionally vulnerable and so different from me. When I do respond, we get our wires crossed, so I try and keep my replies neutral. For example, he had been trying to recruit my young best friend to his crew, and even after I said she wasn’t interested multiple times, he added her and starting talking to her on social media. I got annoyed at him over boundaries and he got in this huge strop about how he could do what he liked. Then he eventually apologised, but the rift keeps widening.

Peter constantly questions how deep our friendship really is, and to clarify, I have always seen him as a friendly work colleague. From my point of view, him pouring out all these emotions on to me seems very strange, as surely he must have closer confidantes his own age? I probably sound quite cold, but I don’t think he should be discussing the legal issues and horrible drama of his break up with me.

I want to maintain our good working relationship, but don’t know how I can enforce boundaries, particularly on social media. Help!

She/her pronouns please. 

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