Dear Captain,
I couldn’t find a similar story, and I don’t know how strong a bro-relation is, so I’ve been quite confused for a while. The history about this story is bigger, but I only want to point out the main things. This is my story:
It all started a year ago, I met this guy Jimmy, which I fell in love with. We became friends. I gathered my courage and confessed to him. The response I got was not what I expected… His reply was just we’ll see what happens. After a month he didn’t took the effort to make it work. We didn’t saw each other at all. For me it was pretty clear that he didn’t wanted to start something with me.
A month later I went to a party at his house. For me this party was the opportunity to find out whether I still had feelings for him. At this party we all drank a little too much and a friend of him, Jason brought me home. I think you can already predict what happened. We kissed, nothing bad yet, except for the fact that this guy has a girlfriend…The next day, when we got sober I talked with Jason, and we decided it was a mistake and never mention it again. I felt horrible for making him cheat, and was so confused about my feelings. So it was easier for me to not seeing them both for a while.
A few weeks later, Jason contacted me. He wanted to see me and I agreed to it. I think I was being naïve, for not seeing what he wanted and we went a step further. His girlfriend still didn’t know anything about it.
A week later I met up with Jimmy at his house. Jason was there too. We talked about cheating and Jimmy hated people who were cheating, he couldn’t understand why someone would do that. At the end of the night he brought me home. We talked and I wanted to know what I meant to him. He confessed that he didn’t want a relationship right now. His ambitions are too big to settle down at this moment, but his feelings towards me can still go any direction. So my secret affair with Jason continued. After a month he ended it all. He confessed our affair to his girlfriend, and he wants to stay with her.
Months passed by without seeing them both, until yesterday. I went to Jimmy’s house, where they both were. The weird thing is that it didn’t felt awkward at all, sitting between them. For all I could say, I got the feeling that Jimmy was hitting on me. For what reason I don’t know, did Jason told him anything? Or is he finally ready to settle down? Just all those assumptions, makes me insecure.
Also I just don’t know what to do if I ever get serious with Jimmy. Am I obligated to tell him about Jason? I still have a weakness for Jimmy, but I don’t know if he can ever accept me for sleeping with Jason and if I would damage his friendship with him.
Dear Letter Writer,
Let me sum up the dudes you are dealing with now:
- Confused cheater guy (Jason).
- Angry guy who hates cheaters and who told you repeatedly that he doesn’t want to be with you (Jimmy).
- Two dudes who withdraw when you are direct about what you want, but then circle back around to hit on you in confusing ways when it’s convenient for them (Both of them).
Let me sum up the kind of partner you deserve:
- Dudes who enthusiastically want to be with you.
- Dudes who are as direct as you are about their desires.
- Dudes who don’t already have girlfriends.
- Dudes who will not show undue interest in your past sex life or shame you about it in any way.
- Dudes who don’t make you feel constantly anxious and insecure.
I think your instincts are telling you something important about how Jimmy is likely to react to finding out about your dalliance with Jason. Right now you are seeing it through a lens of “trying to deserve Jimmy,” so your reaction is all “Oh no, I ruined it” because you are anticipating the slut-shaming that could come your way if he blames you for what happened (even though his friend, the one with the girlfriend, participated fully in things and escalated them later). The way you describe Jimmy, and the subject line of your email “bros before hos,” make it very easy for me to imagine him bringing up the time you slept with Jason every single time it’s convenient for him, like, when he feels insecure or when you disagree about something and he wants to put you in your place. I think the dynamic between you and Jimmy is one where you audition for his affection and he is the decider – “not right now, doesn’t fit in with his ambitions, not really feeling it” – and I understand why information like this feels like an unfair weight on the scales. Let’s be clear: You don’t seem proud of what went down with Jason, and you may have some murky karma as far as Jason’s girlfriend is concerned, or with yourself and your own ethics around cheating, but you were single when all this was going on and you owe Jimmy jack shit in terms of explanations or apologies. If he were to bring it up in a negative light you would be justified in saying “That is ancient history and also what is your point?”
I understand not wanting to stir the pot when things are fun and chill and hopeful again, but I don’t think this thing with Jimmy is going to work out. Not because of Jason, or because you ruined it, but because Jimmy has never really been all that into you and I think this past year has been an exercise in figuring out how little you can settle for. The part of you that asks “Is this person treating me right? Will this relationship meet my needs?” has gone quiet. With all the love in the world, I recommend that you detox from both of these dudes, Letter Writer, until that part of you wakes up and flexes its muscles again. There are better partners out there for you, and you’ll know them when you meet them because they will make sure you know how they feel about you and you won’t have to strategize or walk on eggshells in order to be with them. They’ll have more for you than on-again, off-again scraps. Believe it.
