This is about me (28M) and a friend (27F), let’s call her H. I’m starting to seriously enter the dating game again, and this is something that’s been on my mind since we’re approaching the point where I imagine H might reach out to me again. I’ve talked to my therapist about it but it’d be nice to see some other opinions. Let me give some detailed context.

I’ve been close friends with H since elementary school, but by no means were we ever “best” friends. We have never been each other’s primary emotional support and honestly didn’t hang out too much, but we always kept up with each other’s lives, had long conversations online/ on the phone, and so forth. A MySpace Top 8 but not Top 1, if you will. Throughout our entire long friendship, I’d always struggled with feelings for H. I think it was very much a Tom from *500 Days of Summer* situation — I had these objectively silly Hollywood ideas that somehow we were meant for each other.

H has had a few serious boyfriends; I’ve dated around but never dated someone longer than a few months for all sorts of reasons (including, but certainly not limited to, her presence in my life). Anyway, it took me a while to get my shit together emotionally, but I finally did and told her about a year ago how I felt (and had felt) about her. She’d known that my feelings were non-platonic but the depth and extent of them blindsided her, since we objectively weren’t *that* close.

H’s response was an unambiguous no. She is religious and she needs someone who shares her faith — it’s her most important dealbreaker. I’m an atheist-leaning agnostic, and I could never convert for someone. So us dating is just entirely, 100% off the table. It’s probably worth also mentioning that she’d considered us dating as well, and she’d said she also wished we could have our ‘fairy tale’ romance. So my feelings weren’t exactly unrequited. But, we’re fundamentally not compatible, and she was aware of it, so she was never really *attached* to the idea of us dating.

During our talk, we agreed to take some time and space from each other, and I totally unfollowed all her social media. It was in effect a break up. But we made it really clear this friendship is important to both of us and want it to continue when we’re ready. I started seeing a therapist and just figured out a bunch of stuff by journaling. A little after a month (I realize this is hella fast but I put in a lot of emotional labor), I arrived at a place where I was at peace with her rejection and no longer harboring hope of her changing her mind etc. I let her know that (she wasn’t happy I reached out so early lol, not my finest moment), and basically she said she’d reach out when she’s ready.

I think that might be coming any time soon as the one year mark of our conversation is coming up, which we’d floated as a potential point to resume our friendship. I’m at a point where I know that it wouldn’t be a problem for me to talk to her. So if it were up to *me* and what is good for my emotional health, I would be fine resuming our friendship — maybe while setting up some boundaries on talking about dating/ romance. Of course, *H* will have her own opinions on what she’s comfortable with, but I can’t know until she reaches out.

But for me, the other relevant factor is how my hypothetical SO feels about it. That’s why I posted here. I was curious what people would think is appropriate. For example, I have a lot of platonic female friends and we’ll (occasionally) just talk on the phone or just go on walks for a few hours just the two of us, and it’s totally fine. Frankly, I would have an issue dating someone who is not okay with that. But I think it would be understandable if someone felt uncomfortable about me doing that with H even though I do it with my other female friends, just due to that history.

So I guess I’m wondering what kind of boundaries people would warrant as necessary here. I’ve occasionally thought that maybe this friendship has hit its expiration point and that it’s a liability to both of us — I can imagine H’s future SO might also have a problem with our friendship. But, speaking only for myself, this friendship is really important to me. I’d rather deal with navigating the emotions here to make sure we remain friends in some capacity.

FWIW, I should also add that one year is a long time, and now I honestly look back with amusement on how emotionally invested I was in H and me as a couple. It’s objectively ridiculous and kind of funny (albeit a touch sweet too lol). But on the other hand, it was something that was really important to me in the past (I pined over her for 15+ years!), and it’s shaped my emotional development a lot. So I also wonder to what extent a future SO would even want to know the specifics here. I don’t think it’d be honest for me to just shrug it off as “It’s all in the past so it doesn’t matter” but making a big deal out of it overstates its impact to where I’m at *now*.

Appreciate any comments. If you’re going to excoriate me, please be gentle about it lol.

**TL;DR**: Was in love with close (but not best) friend for many years. Got rejected & moved on, but want to keep her friendship. What do you think is an appropriate relationship for us to have?

6 comments
  1. I think it’s time to move on… but also, & maybe this is just me, but I wouldn’t be cool with my man going on walks alone with his female friends. Maybe if I was close with them too, but in my own experience, no man wants to be platonic close friends with me unless he’s gay. Close guy friends have ALWAYS tried to get into my pants (or admitted feelings for me) so I just don’t trust those relationships.

  2. I think you might be worrying about this a little too much. At the moment, you don’t have a friendship with H — she might not ever get back in touch, right? There’s a chance she might not feel capable of having a friendship after knowing how strongly you felt for her (her anger at you contacting her “too early” makes me think this is a possibility). Even if she does, you’re not in a relationship yet so there’s nothing to worry about for the time being. You guys can just be normal, platonic friends.

    If you do get into a relationship, my advice would be that this story isn’t relevant for your new SO. You never dated H, so it’s not like you’re hanging out with an ex-gf without telling your new SO. Speaking from experience, telling a new gf that you had a crush on someone for 15 years is just going to make her uncomfortable around H (I had this and it was hard for me to shake the feeling that he was still harboring feelings).

    Of course, if you are still harboring feelings for H (which is the only other reason I can imagine you’re worrying about this), I would suggest not getting into a new relationship until you’re over it — it’s not fair to any new potential partner.

  3. If you can genuinely handle a friendship with her and enjoy what she brings to the table as a FRIEND, and not a perspective partner than I’d say be friends. You’ve invested alot into her and care for her, if she’s down to hangout then I don’t see why not. As long as it isn’t a huge downer that she’ll most likely never reciprocate your feelings.

  4. My wife would not like me having a close solo relationship with another woman who is not a relative. Also, you are 28 years old, why are you wasting time worrying about a woman who rejected you?

  5. I think you are putting the cart before the horse. You don’t know if she is ever going to reach out. And frankly you shouldn’t count on it. The sad fact of friendships is that some of them don’t ever survive the dating proposal and rejection, even if you both get over it emotionally. The friendship just isn’t the same and can’t be repaired. I still follow the guy I had a similar experience with – I asked him out, he rejected me – on social media but we don’t ever interact in the same ways we used to. And that’s fine. It happens sometimes.

    As for the future SO, again, you are so focused on H that you are already overanalysing future boundaries with regarding her and your possible SO. I think any girl dating you would be kind of weirded out by being told, “hey I have this friend and I used to like her romantically but I am over it and she might reach out soon and you have to be okay with us being close friends again”. Of course you can have female friends. Of course you can even be friends with exes or former crushes. But you are kind of putting the potential friendship (that still might never resume) over your potential relationship with a new person.

    So why not focus on dating for now. Look for a person you are compatible with, who you have fun with, who you are attracted to. Obviously jealousy is a red flag but if you focus too much on this (frankly past) friendship with H you will make a girl jealous, because you are prioritizing somebody else ahead of her. So focus on whoever you end up dating instead and hopefully you find somebody wonderful to be with.

  6. Its not healthy to be friend with someone you have feelings for. You will get upset. Why put yourself though that? Just end the friendship and move on.

Leave a Reply
You May Also Like