Finding myself (36M) in a weird situation. In the town where my second home is, I’ve been friends with someone (34F) for a few years, but until last Summer they were on the periphery of my friend circle. I honestly had never considered her someone I’d want to date or be intimate with – we were just that different. I will say I have always found her to be good looking, so the tale below isn’t some kind of desperation play or me settling.

We started hanging out more and getting to know each other better, and somewhere in the blur of the past 12 months, we began to talk to each other on the phone almost daily.

Very recently we went on a trip out of town – I flew from my actual hometown and she picked me up at a nearby airport – to meet some of her family members. Trip was a success, I got rave reviews from the relatives (so I was told). We road tripped home together back to my primary home, which added 3 hours to her journey but she knew that going in to the trip and was okay with it.

I realized that weekend that I actually was developing feelings for my friend, and told her that I liked her when we got back to my condo. She acknowledged it and said that for now, she wants to be friends as she’s working through a lot of personal stuff at the moment, and any sort of relationship is out of the question for now, “but if we end up having sex at later point…whatever we gotta do to keep things fun.” Which I’m okay with. She has had to put me in my place a couple times when my flirting got a little too aggressive for her comfort…and I keep telling that I’m glad she’s setting those boundaries (an area of struggle for her), as emotional dysfunction / coming off very strong is a huge issue for me with women I like.

Late last week, I decided on somewhat of a whim that I wanted to come up to my second home for a couple weeks, and we’ve been getting together at both of our homes and at mutual friends places as well. While we’re not all over each other (ie spooning or cuddling), I do make subtle moves to keep myself physically close, whether its grazing her knee while we’re sitting together or light touches during conversation, which are reciprocated equally. We have also spent pretty much every day together since I arrived, and have plans laid out that pretty much mean we’ll be spending a lot of time together in the days/weeks ahead. We’ve also talked about longer term plans including possibly traveling abroad later this year.

All of these things I see as pretty strong green flags to keep doing what I’m doing, but remembering to keep it in the context of that we are just friends right now, and nothing more.

There is a yellow flag out there however. Her ex (37M) is a really close friend of hers, and is becoming a good buddy of mine – they have a similar rapport to us. I am convinced that they are in a situationship, but I know that’s not my business nor my place to interfere with it, if they are. He told me (before I had feelings for her) that he wants to get back together with her, and she has also told me that they’ve talked about it – with her rebuffing him in a similar manner to how she rebuffed me. Being the cautious person I am, I want to continue getting to know my 34F friend better, but at the same time I don’t want to be labelled as the out of towner who steals women from the local men. (I plan to take him only out to lunch later this week and hope to talk things through, just so he isn’t caught off guard by my pursuing of his ex.)

I expect that it will be at least six months of us in this friendship with me pushing for more, but it could be longer. Or we could never advance things to an intimate level. Who knows.

Am I just wasting my time, perhaps I should focus on meeting someone in my hometown and cherish the friendship I have? How many of you out there have successfully converted a platonic friendship into more than friends? Thanks.

14 comments
  1. Honestly, speaking as a guy who *just* got done seeing someone who had a close guy friend, you’re all just setting yourselves up for failure and drama. I don’t know how secure you are as a person, or what your lady and her ex’s dynamic is, but the woman I was seeing was driving me insane with the way they would act around each other (they weren’t even exes) and that was just related to the things I had eyeballs on. She saw nothing inappropriate with their behavior and refused to implement any sort of boundary on my behalf.

    That aside, she’s also not giving you the enthusiastic and receptive response towards starting something that (I feel) she should be giving you. You say that this isn’t a desperation play, but are you actually involved in your local dating scene, or is this one of those things where you’re desiring companionship but not putting in all of the work over going out and meeting someone new, and she just happens to be around? Because I’ve been there.

    The way it’s written is unclear, but just to clarify, her and her ex live in one place and you live in a separate one? I think you should put your feelings aside in this case and write the situation off as soon as possible. Stop trying to slowly lead her into something that she seemingly doesn’t want to do. You don’t have to stop being her friend, but you need to admit to yourself that the chances of your pursuit turning out well for all three of you (or even just 2/3) are extremely slim.

  2. First I was going to say that you were reaching a bit and going to ruin a friendship but when she picked you up at the airport, that means something 😂

    Then you talked about the ex..so another plot twist.

    So I say screw it, just invite her out once and see what’s what. Please update us.

  3. I would say, as a woman, she has already set a boundary for you and you keep crossing it. She told you she wanted to be friends. I don’t let my male friends continually be physically close to me. I do not believe she has romantic interest in you at this point and, especially if she is still working through issues with her ex, you need to let that go out of your mind.

  4. Not only are you wasting your time, if you continue down this path it will likely cost you your self respect and confidence at some point. If you can’t get rid of the feelings completely, then the best you can do is give her a hard ultimatum, which sounds like is a no currently, for trying a relationship. Walk away and if she comes back later you’ll at least know you’re not being strung along. Pushing to get out of the friend zone for even one month is too much. Walk away. Run away. You can give her the ultimatum if you want, but you know the answer. Your dignity and confidence will thank you later.

  5. Dang that’s a lot of work. You’re a trooper for pursuing this, to me all her signs seem to point that she’s holding you back from making advances because she does not see anything there with you.

    Could be she is infact seeing her ex, in the end it doesn’t matter because she’s layed out boundaries that clearly distinguish you as just a friend who sometimes gets flirty.

    No need to abandon the friendship but set your eyes on someone who can reciprocate what you’re giving out. You deserve better

  6. So she said she wasn’t in the right space to date you but threw out the considerable carrot of ‘maybe we can still have sex someday though’. Then she proceeds to ‘put you in your place’ when your flirting gets too much for her.

    If timing actually was the reason on her side and she did genuinely see you as a romantic option down the road then she certainly would not be toying with you like this. It just conveys a lack of respect. She lets you graze her knee from time to time? None of the things you mentioned are supposed green lights for a relationship…this is extreme wishful thinking on your end. OP is so deep inside the friend zone right now that he can’t see daylight. If he continues down this path then it’s unlikely to end well for him.

    OP needs to honestly ask himself if he’d be OK with continuing to spend this huge amount of time with her but never actually getting together with her or more likely having to watch from the sidelines as she dates and sleeps with other people. If the answer to that is no, then he needs so start reducing the amount of time he spends with her. And for goodness sake, see other people! The chances of you getting with this girl are slim to none. And the longer you keep hanging on her every word, hoping to make her change her mind about you, the lower her romantic respect for you will fall.

  7. I’ve been in your shoes to some extent. Here’s my take.

    She’s a friend who likes your attention because it makes her feel good about herself and it provides a validation and dopamine boost.

    She doesn’t see more happening with you hence the setting of boundaries that you seem hellbent on ignoring. She told you this when you confessed your feelings.

    Treat her as a friend and keep it that way. Wearing her down while she leads both you and her ex on isn’t a strategy that is going to end well for anyone.

    You shot your shot when you told her you had feelings and she said “thanks but we’re just friends”. If you can’t move back to a normal friendship you need to stop seeing her (either a big break, or severely reduce the frequency) or you will drive yourself crazy.

  8. You’re not wasting your time. But consider the number of opportunities you’re ignoring by focusing your energy in prioritizing someone that wants to be friends.

    You would only be wasting your time if you only looked at this opportunity and ignored everything else around you. You should be looking and dating and if the timing is right this woman and you may find that space to connect in the way I think you prefer-not as friends but as a couple.

  9. She has made it clear on a number of occasions that she is not interested in more than friendship. Your friend shouldn’t have to put you in your place a couple of times. No once should have been enough. If she is interested in changing the dynamic, she needs to be the one who does it. Accept it is a platonic friendship and focus your attention on dating someone else.

  10. She told she’s working through things right now so you just need to respect that and give her space so she can work on herself. In the meantime, see other people. It’s true that friendships can turn into relationships, but you’re pushing the issue and she has already set boundaries with you. You need to respect them.

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