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Hi Captain Awkward,

My partner [26M] and I have been together for about 6 months. We both genuinely love each other, and have been telling each other that we love each other for the last few months; but some recent events have led me to reconsider how seriously committed he is to the relationship, and how much I can trust him.

All of this started about two months into our relationship, when he invited me to his roommate’s brunch at his apartment. He introduced me to a friend of his at the brunch, let’s call her Sophie. It was immediately obvious to me that they shared some sort of a romantic history, for the following reasons: 1) Sophie felt comfortable flirting with him in front of me, 2) she wouldn’t make eye contact with me when we were all engaged in a conversation together, and 3) she made a rude joke about me during this three-way conversation that was frankly quite demeaning (accusing me of being afflicted by a psychological syndrome). I didn’t say anything to my partner at the time because we just started dating two months prior (and I didn’t want to come off as jealous/possessive/controlling), and we hadn’t officially talked about being boyfriend-girlfriend yet (although other events at the brunch sparked the wonderful conversation which resulted in us making it official, two days later). So I decided to brush it off.

Fast-forward about two months later. My boyfriend kept inviting me to parties/get-togethers that Sophie was throwing, and I kept declining. (I gave excuses, but I should’ve been forthright about the fact that I didn’t want to go to an event with someone who I suspected he shared a past with, and who felt comfortable flirting with him in front of me). He ended up going to her birthday party one night. When he came to my apartment later that night, I finally built up the nerve to confront him about whether or not they shared a past. He said yes. Here are the many red flags that popped up during my partner’s recounting of said party:

At this party, her and her friends filmed a movie reenactment, including a scene where my partner kneels down on one knee, grabs Sophie’s hand and kisses it tenderly. My partner showed me this video with pride and laughter once he arrived at my apartment later that night. Important note: Although there were many parts to this video (approx. 7), which all appeared on Sophie’s Insta story that same night, the only part of that story that she *permanently posted to her public Instagram profile* was the video of my partner kissing her hand.

My boyfriend revealed to me that they spoke at the party about their (almost) romantic past (they went on a date and almost hooked up once on a separate occasion, but they never pursued anything because Sophie was “interested in something casual” and he was “interested in something more.”).

Sophie asked him if he “made me his girlfriend yet”, to which he said yes; which was followed by “are you two exclusive?”. When my partner said that we were indeed exclusive, he explicitly reported that Sophie reacted in a “disappointed way”.

Just before my partner left the party, Sophie grabbed his phone and sent me a selfie of the two of them together (despite my not knowing her? It was strange.).

Breach of trust #1: Not telling me about his romantic past with this “friend” of his before inviting me to multiple events that she was throwing

After this all happened, my partner and I had a long conversation about boundaries. I explained to him that it makes me uncomfortable to be around people he shares a romantic history with; and that, because I’m the kind of person that prefers to remove myself from situations where I feel uncomfortable, I *need* to know this information before making a fully-informed decision about whether or not I want to show up to a social event with said person. (I can’t very well tell him who and who not to be friends with; all I can do is decide where I want to go and who I feel comfortable surrounding myself with). I also explained that Sophie’s behaviour was especially problematic, because she feels comfortable actively flirting with someone who she knows is in a relationship (not to mention– flirting with someone who is in a relationship [my bf] *in front of* the person they’re dating [me]).

At the time I thought the conversation went really well. My boyfriend was receptive to what I was feeling and saying, acknowledged that Sophie was indeed flirting with him, and promised to tell me in the future when invited to a social event if someone he shares a romantic history with would also be there. Everything seemed to be going well until the last couple of weeks, especially until last Sunday…

Some context is in order here: my grandmother passed away two weeks ago, and her funeral was last Saturday. I also found out that I was pregnant the morning of last Sunday (I’m getting an abortion). I was out of town for the last two weeks to help with the funeral and such, and during this time my boyfriend fell into radio silence. We did speak every now and again, but he was far from supportive during this time. Even worse, when the test came out positive, he waited three hours before contacting me; and when he did, he didn’t even acknowledge that the test was positive.

Okay, back to the main narrative: on Sunday afternoon, I received a notification that I was invited to my boyfriend’s birthday party. I checked the invite list, only to find that Sophie had already clicked “going” on the event.

Breach of trust #2: Invited Sophie to his birthday party (which indirectly uninvited me) *despite* me telling him that being around Sophie makes me feel really uncomfortable [context adding insult to injury here as well].

I was pretty devastated to say the least (and especially, in the context of grieving the loss of my grandmother and having to deal with an unwanted pregnancy). I called him that night to explain to him why I felt hurt, disrespected, and disappointed. I explained that I would not be attending his birthday party, because his inviting Sophie indirectly uninvited me. I explained that this shouldn’t be a surprise to him, because we had a conversation explicitly about this and explicitly about her. I explained to him that I was hurt because he was prioritizing his relationship with Sophie over his relationship with me. (I can go into more detail about the conversation we had in the comments section if need be).

Anyways he apologized, and went so far as to cancel his birthday party (which I thought was a bit drastic, but OK it’s his decision). He’s since seemed to *actually* realize how inappropriate Sophie’s behaviour was, and has admitted that “he didn’t want to see the bad side of her behaviour when I first brought it up because he likes to see the best in people.”

Breach of trust #3: Less than a week after the birthday party fiasco, after I explicitly asked him not to tell his two male friends about the pregnancy, he told them anyways. He (again!) apologized after the fact, but this is another installment in a set of trust breaches that has sounded two many alarm bells in my mind.

Part of me thinks that my boyfriend is actually interested in Sophie, and that’s why he’s been enabling her flirtatious behaviour all of this time (despite saying multiple times that he isn’t interested). But part of me also knows that I’m thinking these thoughts because I have lost trust in him, and I don’t know how to rebuild that trust. I’ve had a conversation with him about open communication, teamwork, and honesty in relationships since BOT #3. A huge part of me, the “pessimistic” side I guess, still doesn’t believe that he’s going to put in the effort to change his behaviour and to become more trustworthy a boyfriend. That’s why I’m here… for advice on how to think and how to act going forward in this situation. I’ll provide more details in the comment section if need be, don’t feel shy! Thanks all in advance.

Sincerely,

A Confused 23yr old she/her

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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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still frame from Disney's Beauty and the Beast

This is a sweet story about a man who had both self-loathing and wealth who coerced a young woman into living with him until such time she could develop Stockholm Syndrome and consent to marriage.

Hello Captain Awkward,

I have an issue that you probably don’t get every day. I have a problem with wealth and dating. I’m in my late 20’s, and I have had the good fortune of becoming quite wealthy. Unfortunately, I am having trouble finding women who like me for me and not my wealth. Back when I was a poor student, I never thought this would be an issue, but it is. I believed that money would solve all my problems with being awkward and feeling inferior and not being able to get laid, and it did help with a lot of those things. It has made finding actual love and good relationships much more difficult. I don’t fit in with the dynastic wealth crowd, and I know there are tons of great women who grew up with money and are not in any way impressed by mine, but I just don’t fit in with that group of people. I have been trying to figure out how to navigate this issue, and it just blew up in my face.

I was seeing a woman for 3 months, but I was lying about my wealth. I have a small apartment in the same building as my real apartment, so I can try to get to know women without getting entangled with the ones who are just with me for my money. It is the sort of apartment that says, “I’m doing well, but I’m no rich guy.” Last week, I decided to come clean, and it did not end well. It was the first time where we went out and I was living life as I live it when I’m not worried about what people are going to think about my money. She thought it was this special occasion because everything was stepped up considerably from our usual dates. I tried explaining that really, I was maybe not being so honest about my income, which she didn’t believe until we came back to my actual apartment. She was furious, and I can understand it. She went on at length about my deception, not trusting her, and treating her like a potential gold digger.

It is true, but I don’t know what else to do. She won’t talk to me, and I think our relationship is probably over. How can I find people who like me for me while living a lifestyle that clearly shows how wealthy I am? I have been burned before both with friends and girlfriends who I thought liked me for who I am but turned out to be interested in being close to someone who is doing well. I have reined in my conspicuous consumption a lot in the past year and a half, but I like having a very nice apartment, I like dressing well, and I like having a nice car. I feel terrible about feeling sorry for myself because this is a problem almost everyone would be envious to have, but I am very lonely.

Sincerely,

A Good Problem Is Still a Problem

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