I’m (18F) seeing somebody at my university (19M). We’ve been home for break for a hefty 6 weeks and will return 5 days from now. Before this hiatus, we had been hanging out for around a month. Great chemistry, would sleep over my dorm over half the time. Love spending time with each other. The day before we left, he asked to be exclusive (not technically dating, but agreeing to not see other people at this point). I said yes. We have talked throughout every single day of break and gone to sleep on the phone 9 nights out of 10. I’ve asked what he wants from me and he says he’s looking to progress the relationship further once we’re back together in person. I felt the same! Yay!

Here’s the thing. One night we were talking about our histories and I told him about a relation that I’d had with somebody (L) with some minor details. Pretty much just that I thought I was in love and he (L) totally rejected me before AND after initiating sex with me. And I was pretty sour about it. It was only around a month before I met this new guy. And the big thing about this whole situation is that he (L) was, and remains to be, one of my closest friends in college. I no longer have any feelings for him, and he is no longer pursuing me by any means. Things have been purely friendly since late October/early November. We had sex one time, agreed that we were better friends than lovers, and moved on. But I feel terrible about all of this. I have a sweatshirt of his, he has a jacket of mine. We did a little swap because we both liked the others’ more. I still wear this nearly every day, since there’s no association of him GIVING it to me in a romantic way. It wasn’t like that. Nor was me giving him my jacket supposed to be taken as a romantic gesture. But he wears that every day, as well.

I’m going to give L his sweatshirt back and ask for my jacket in return, for sake of my new partner’s comfort. I know now that I should not be wearing it. But I’m imagining a scene in my head where they meet and L is wearing the sweatshirt that my new partner has seen me in so many times. He has even tried it on jokingly and then taken it off. This had my stomach churning with guilt. I’m unsure how to approach this whole situation. I do not want to end my friendship with L.

I do not feel comfortable lying to my new partner about me and L’s history. And I am planning on telling him, because I would want him to tell me. He hasn’t given any signs of being controlling and whatnot. But I do spend a lot of time with L as he’s very important to me – but I am not looking for anything more than friendship. And I have been nothing but loyal to this guy. And he knows that. But I would hate to upset him for no reason. Does anybody have any advice? How should I approach the conversation? In my head I should definitely bring it up, just so he doesn’t question things at all. I feel that getting ahead of it is important to avoid any misunderstandings. Am I wrong? Or overthinking? Is it worth mentioning at all, or will it simply make things more complicated? Thanks in advance!

6 comments
  1. I think that you should tell your partner. If he’s the person you’re looking for a long term relationship with, it might as well be a litmus test!

  2. You’re overthinking it. Give the sweatshirt to a homeless person or resale shop if you feel bad. You’ve had feelings for L in the past, so you should distance yourself, at least a bit. It is very likely that when he sees that you are into someone else and unavailable that he will “suddenly” realize the feelings that he has had for you “all along.”

    What I am confused about is what you need to tell your new BF that you haven’t shared already?

    >One night we were talking about our histories and I told him about a relation that I’d had with somebody (L) with some minor details. Pretty much just that I thought I was in love and he (L) totally rejected me before AND after initiating sex with me.

    What else is there to say?

  3. Carefully and with full knowledge and acceptance that usually you’re going to end up having to axe one of them.

    >Pretty much just that I thought I was in love and he (L) totally rejected me before AND after initiating sex with me. And I was pretty sour about it. It was only around a month before I met this new guy. And the big thing about this whole situation is that he (L) was, and remains to be, one of my closest friends in college.

    Well, you’re poisoning the well by doing that, but that is your prerogative.

    ​

    >I have a sweatshirt of his, he has a jacket of mine. We did a little swap because we both liked the others’ more. I still wear this nearly every day, since there’s no association of him GIVING it to me in a romantic way. It wasn’t like that. Nor was me giving him my jacket supposed to be taken as a romantic gesture. But he wears that every day, as well.

    You’re 18. Being naive and learning from the mistakes that result from that come with the territory. Just don’t beat yourself up about it.

    ​

    >And I have been nothing but loyal to this guy.

    While nice, that also doesn’t count for as much as you think, given the nature of how you were apparently taken advantage of by L, there’s very little reassuring here that you wouldn’t change your mind and give him another chance if he changed his mind and said the right words to you.

    ​

    >Is it worth mentioning at all, or will it simply make things more complicated?

    It’s pretty important information that you need to be the one to disclose. It’s ***also*** going to make things more complicated, especially if you insist on trying to keep both men in your life.

    But if you try to hide it and it then comes out, things will explode quite spectacularly.

  4. <preparing for the downvotes>

    I can’t speak for all guys but for regular dudes like me (ehh..”traditional”?), we can’t stand our girlfriends/Wives having “guy friends”.

    We may not say it, but deep down, we’re uncomfortable with the idea because we know what guys do and think, because we’re one of them.

    Call it being insecure, but it’s baked into us at a primal level. So let’s say you never slept with that friend and it was all above board…it feels all the same to your BF.

    Pick one of the two guys you’re mulling over and ditch the other. You can’t have both in your life. It sounds like one isn’t really that into you as a GF, so it should be an easy decision.

    Or not. Because the BF will find out eventually (and boy, he won’t be learning it with the correct context!!), which would devastate any trust he had with you.

    .

Leave a Reply
You May Also Like