Tag Archives: Relationships

Hello Captain Awkward,

I’m feeling quite stuck in a romantic situation and am hoping you can help.

Last year I took a job in a town 5 hours away. To my surprise and delight, a co-worker who I had a secret crush on messaged me daily after I left and from there she admits she is attracted to me. Problem being, she is married. The texting gets intense- sexting 24/7. After a few weeks, I drove up to the city and we spent the weekend with each other, in bed together for most of it. She was racked with guilt, I felt guilty too and also guilty because I had feelings for her and she insisted no feelings were to be involved in this. Guilty feelings made way for more and more of these weekends and trips together- we saw each other most weeks despite living in different cities, having an intensely passionate and sexual relationship for over a year.

I didn’t want to sneak around forever and wanted more of a relationship. She told me for months that we would have that, and she was in the process of separating. However one day she announces she can never leave him and get a divorce. Also, she doesn’t want to disappoint and be disowned by friends and family. I was upset but carried on with the relationship because I just didn’t have it in me to leave.

Before we got together, she had planned to live overseas and travel. I would get upset as the time loomed closer when she was due to leave, just as we were getting serious. She reassured me that it was for the best- a way of separating from her husband so we could together. Yet, only a week before she left, she informed me that he had taken a job over there and was going with her. Nevertheless, she insists they aren’t really together, just friends and she will come back to be with me in a year’s time.

I was upset and angry, although accepting that I am ultimately responsible for my own unhappiness about it because I did get involved with a married woman.

I am still in love with her and want to be with her. However I know it’s best for me to leave this all behind. Yet every time I do, she guilt trips me so hard into staying and staying in contact while she is over there- making it impossible to move on. I was hoping Captain that you would be able to shed some light on an escape route out of this and some potential scripts for when she guilts me into staying.

Thanks heaps,


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Dear Captain Awkward,

I’m currently over 2 years into a poly relationship with a wonderful person. Our policy is that we’re both free to have casual sex, and we’ll treat dating people on a case by case basis. The majority of our relationship has been long distance, but I very recently moved to live a few blocks away from them.

Partner has a friend who was also known them for as long as I have. Over the course of our relationship, they’ve grown very close. Every time I heard about Friend from Partner for the first year or so, they kept assuring me they were “just friends” and that they’d never be interested in anything more with him, even though I didn’t ask for that assurance.

Then, Partner asked me if they could do nonsexual kink things with Friend, which I was okay with. This came with more assurances that they’d never be interested in doing sexual or romantic things with him, again without me asking for them.

Early this year, Partner asked to start dating Friend. I said I wasn’t comfortable with it right then. Partner asked again a month or so later because Friend’s partner decided to open up their relationship. I said I needed to wait until I lived near Partner and see if I felt more comfortable in our relationship.

Over the summer, Friend visited Partner and they had sex, even though I told Partner I was uncomfortable with that. They apologized for being inconsiderate of my feelings, saying that it just happened. A day before I moved, Friend’s new partner referred to Partner as their “metamour” in a place where I saw and Partner brushed it off as a misunderstanding. After that, I told them I wasn’t sure I’d ever be comfortable with them dating Friend while still dating me.

It’s now been two months since I moved and while my relationship with Partner is stronger than before, I’m still not comfortable with them dating Friend. They’ve given some hints that they want to talk about this sometime soon, but they haven’t brought it up yet.

Other than this issue, I am really in love with Partner, although I still don’t feel like I’m getting enough affection (school and health issues make fixing this hard).
I don’t know how to get over Partner giving specific boundaries for their relationship with Friend and then changing them suddenly.
Thinking about this situation makes me have anxiety attacks and cry. I’m working on finding a new therapist, but it’s hard having just moved and needing to find a bunch of new doctors.

Am I being ridiculous about this whole thing? What do I do when Partner brings up the subject again?

– Too Anxious, Too Needy

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Dear Captain Awkward,

So… Not sure if this fits under relationship advice or under the “how to be a regular human being and not a lizard person” category. I’ve been seeing this guy for the last 10 months. He is great, but I’m the first person he’s actually gone out with since ending a long, traumatic and when we met he said he wasn’t looking for commitment. I was fine with it, but then we kept seeing each other and I started falling hard and wanting more – to actually be able to look forward to things and not just treat every encounter as “oh, this could or could not have happened, what random happenstance”.

The thing is, although he’s said he’s in love with me and wants to try being with me, he’s still unable to make plans. If he says “see you saturday”, that doesn’t mean we will definitely see each other saturday, but rather that when he said it it sounded like it might be a nice idea. Come saturday, though, he might decide to go do something else entirely and fall off the grid whilst I’m waiting to hear from him. As someone who has a limited amount of energy for social interaction and a few anxiety issues, I treat planning as something serious. If someone says “see you saturday”, I expect to hear from them saturday. Now, I realised he comes from a different perspective and it’s better to check things on the actual date and not count on them as solid plans, but it still wears on me a bit.

It’s like..Though I know plans could change at any moment, things happen, feelings change, life is unpredictable… And if he changed his mind I would try not to hold him against it… I still feel like I need a plan? Even if it’s not ironclad, just knowing that right now there is a more likely outcome or a desired outcome would make me feel more secure? Does that make sense?

Also, he’s seemed a bit distant lately (still texts almost every day, actually came to see me and brought medicine and food over because I have a cold – but left after sex saying he needed to go home and we MIGHT see each other later… or, you know, not) and I’m not sure if it’s just my insecurity or indicative or something a bit more worrisome. Anyway, my point is: despite thinking of several reasons to work around it (“the distance is all in my head” and “who needs plans anyway”) I keep feeling a bit neglected and anxious. I’m thinking of ending things, not because I want to – I love the guy and he seems to care for me back – but because I think I handle being lonely better when I’m alone and it might be less stressful.

I’ve tried talking to him about it, but he says he’s like this in general, not just with me and there is no point in treating plans as solid because the future is such a changeable thing. So, how do I make peace with being in the moment and stop worrying bout unreasonable things? If there is no ironclad future, how do you stop yourself from having expectations? And how to manage a schedule with someone who doesn’t believe in plans?

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Ahoy, Captain Awkward!

Looking for some relationship advice and hoping you can help.

Background: Boyfriend and I met through a mutual friend, I’m in my mid 20s(first serious relationship) he’s in his late 30s(and been around the block a few times, though never married). It’s been an awesome two years and we’re looking into moving in together(though for the record, I haven’t slept in my own bed since March and it’s now July). I’m excited about the whole situation save for one major issue; his ex, M.

M and boyfriend basically grew up together and have always been very close. They dated for a couple years but broke it off because (according to him) it was too much like siblings dating.

She has a history of serious panic attacks and boyfriend seems to be the only one who can calm her. She was suffering so badly at one point that her baby daddy got boyfriend a job in their state(2 states away from where boyfriend was living) to help calm M down. While this was all before my time, it always struck me as odd that they were all so close.

M has always had constant contact with boyfriend the entire 2 years we’ve been together, whether it be emails, FB posts, texts, calls, kissy emoticons, etc. And now with another wave of serious panic attacks brewing, the phone calls are getting more frequent and the visits more lengthy. I’ve talked to boyfriend about maybe suggesting professional help for her as M’s constant contact is taking its toll on him(to the point where he says he’s exhausted and he’s starting to freak out a bit just listening to her freak outs). But he brushes it off with “People who’ve never suffered don’t understand” and “She’s family. I can’t just ignore it”.

Don’t get me wrong, M is super sweet but it also feels like she’s co-dependent on boyfriend and he either doesn’t see it or just chalks it up to being “family”. M, baby daddy and co have since moved back to their home state (5minutes away from boyfriend). And having been here for 3 or so years, M has yet to make any friends of her own, hence the tight hold she appears to have on boyfriend to help her deal with things.

All that to say, what do I do? I love boyfriend and I’ve always heard you marry the man, you marry the family, but am I wrong in thinking this is too much family? I want to build a future with this man but I don’t know if I’m ready to build a future with him AND M. Previous relationships he’s had he said “worked” because the women were “mature” enough to understand the relationship he and M have. So am I not being mature enough? Do I try and make some sort of ultimatum? Break it off til he gets his priorities back on the relationship?

-Sidelined In California

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Letter Writers, no one is topping “Dear Sugar” on this topic. Read that and you’re probably good. But just in case, your letters and some answers are below.

Dear Captain Awkward:

I’m 29 and female, and have been in a relationship with the same guy since college. We now live together. He wants to marry me. I have no objections to him as a person, like spending time with him, and have many interests in common. 90% of the people I talk to socially I have met through him.


I’ve found, as I’ve lived with him, that I really do not enjoy living with him. A large part of this is due to the house he owns, which is tiny and cluttered and dark and damp, and whose appliances (oven, shower, washer) are constantly breaking. He doesn’t have the money to move; I have even less money than he does.

I also have very little interest in sex (this may be due to depression, which is an issue I’m getting therapy for), and although he has been good about this, I’m beginning to be a bit creeped out by the fact that he keeps pointing out to me, unsolicited, how he doesn’t want to push me into having sex before I’m ready. Uh…Great? (A similar thing that’s also starting to scare me is that although I’ve told him I don’t want or particularly like children when it’s come up, he keeps telling me I would make an AWESOME parent. A lot. Unsolicited.)

The last time I tried to bring up the above problems and explain to him that I didn’t want to be married to him, didn’t want to live with him, and had no interest in either sex or children, he begged me to “work this out”. I agreed, and am now super angry with myself for not sticking with my guns.

…What do I do? I do genuinely enjoy doing Friend Things with him, I just don’t want to be his wife or his live-in…whatever. I also don’t want to be talked into sticking around any longer.

Possible Awful Bitch

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Willow and Evil Willow from Buffy Season 2

Willow, talking about Evil Willow: “That’s me as a vampire? I’m so evil, and skanky…and I think I’m kinda gay.” 1) How has this image never come up at the blog before? 2) Don’t marry off just one of the sides of yourself and kill off the other. They’re both you.

Hi Captain:

I have been in a relationship with  my boyfriend now for 5 years. I met Leigh when I was 19, fell in love, grew up together, and last year bought a house together; we even had an engagement ceremony so our family would feel more at ease with us living together. Even though it was just a front, Leigh already sees me as his fiancé. I think you know where this is going. 

Last year shortly after we purchased our first home, I met a guy through an online game. Jack fell in love with me even though we have never met each other in person. We texted each other day and night for months and eventually things got progressively worse. We started “sexting” and it was then that I started living in guilt, every living moment. I sleep talk when I go to bed at night, and it didn’t take long until Leigh found out that I was cheating on him emotionally. I knew what a horrible person I have been and hated myself for enjoying having intimate conversations with Jack. Most of the time, I felt downright disgusted about myself. I stopped talking to Jack, and he continued reaching out to me telling me he needed me and can’t live without me. Jack texts me every 2 weeks to tell me that he trusts me and will always be there for me but I’ve ignored them all, as I believed he was a temptation I have to stay away from. In order for me to salvage my relationship with Leigh I need to fully devote myself him and one day we will get married and have kids and live our lives like all the loving couple in the world. Leigh being the perfect man that loves me more than anyone in the world, he forgave me and decided to trust me again. 

I travelled solo as a backpacker just last week and made out with a girl and a guy that I met at  a bar. I almost had sex with a guy I met at the hostel but I didn’t for I know I am in a relationship. I despise myself for even having the horrible thought and genuinely enjoyed being hit on by them, having them telling me how beautiful and sexy I am. I had the time of my life when I was there, for once feeling as though I am single.  I thought I could just forget all about it once I get home, and concentrate on being the perfect girl friend again and wait for the feeling of wanting to be single to go away. Sleep talking didn’t help, as Leigh found out in my sleep that I have been apologising “for being a whore” and that “I’m sorry, I’m wrong”. He also managed to find a conversation of me and a friend regarding this situation. The guilt is eating me alive but I didn’t know what else to do. Leigh left me this morning, to travel by himself and to give me time to figure out what is it that I really wanted. He is willing to put a hold on this relationship and let me leave and “find myself” and “do whatever I want” as long as I don’t tell him any of that when I come home. I am with a man that loves me so much, enough to forgive me from cheating on him and would sacrifice everything in his power to make me happy. What more do I want? Am I really willing to let a man like this go just to fuel my desire of being single?


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Dear Captain Awkward:

My 27 year old son has been in a relationship with his girlfriend for about 18 months. He was living with a friend until a couple months ago, when he and his girlfriend moved to an apartment. Before the move, his friend came to see my husband and I to talk about the situation. He said that the girlfriend is a total loser and the two of them fight constantly. He said many of their friends can’t stand her, and that the two of them drink and smoke weed, i.e. enable each other’s recreational drug use. They are both broke most of the time, although they work full time at low level jobs. My son was barely able to cover living expenses before, and asked us for financial help from time to time. When we heard about his plans to move in with her, we were not happy but came to grips with the situation, accepting the fact he is an adult and has to make his own decisions. Since then, we have stopped all flow of cash to him, hoping the living situation and the relationship will eventually fall apart and he will start over.

We do not want the girlfriend attending all our family gatherings. It’s too stressful for me to converse with her because I feel she is a terrible influence on him. The problem is, she’s manipulative and puts on a very phony act around us. I see right through her, as my son can also be that way. I can see how they feed off each other and it drives me crazy. She seems to rule his life and is very self centered. I’ve wondered if there is some sex addiction going on, because for the life of me I can’t understand his attraction to her otherwise. I just see a toxic relationship, like his friend told us.

I am struggling with how to handle a family gathering at Christmas. She was with us at Thanksgiving and that was too much for me. Should we tell him it’s family only, or should I just decline to attend????

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