Question about woman I used to date and now friends with

[SoloD]

There is a long back story. I hope you will bare with me.

I am a 45 year old man, and I keep in touch with a woman I used to date at university.

I use that term loosely. We dated 7 times over 5 years for probably an average of 3 weeks each time. Each time she broke it off, we remained close and eventually started again. I was besotted by her back then, but immature and let's face it, insecure and not much to offer

The final time we dated I had a realisation than I was getting too obsessed and I needed to move on, as this was not healthy. Which I did. I married, had children but we sort of kept in touch and would have lunch every few years to catch up.

I moved abroad, got divorced, my son is now 17 and came back to the UK and lives with my sister to go the do his A-levels in the UK. So I have been more frequently in coming back.

I have thus got into the habit of seeing this girl more frequently. She is single, never married and is very successful career wise, more so than me, though I have done reasonable well.

Two years ago while I was in the UK, she sent me a photo of a shop we used to go to and some comment about it. I responded by saying I missed her, she asked why and I told her that I could explain but needed to do it face to face and could I come and see her. She said she was busy that evening and the following evening. So I took that as a hint. That is fair enough.

I was over in February, she invited me to her new house and invited me to stay the night (in spare bedroom). We had a nice time just talking, her showing me her holiday photos etc. after she went to bed, I did need to ask her for some loo roll as there was none and the look on her face when I knocked on her bedroom door suggested to me that she was worried I was after something more.

Saw her last week, again she invited me to come and stayed over in spare bedroom. We met in London and took train, did a walk, stopped for dinner, she showed me the places she likes to go, including under a weeping willow tree which she described as romantic. I made her laugh so much she couldn't breathe for a minute.

I am curious to know her perspective. She keeps in touch with me, she sends we pictures and videos of herself, we have what I think are great times together. I clearly would love to date her again, I feel I connect with her more than anyone I have ever known.

But on balance I don't think she feels the same way, and I don't want to do something stupid. I value our friendship more than I can express.

I would really like to know what she is thinking. Has anyone got any insights?

If you feel that way about her, it doesn't really work for you as a friendship so I don't see what you have to lose by asking her out? At least then you'd know where you stand.

You using the word "obsessed" does suggest a bit of projection onto her as your ideal woman, though. You might be surprised!

I think you have to ask her don’t you? It’s the only way you will know her true feelings and, while it might put the kibosh on your friendship, it’s incredibly hard to be friends with someone you have feelings for and that aren’t reciprocated.

She enjoys you worshipping her and you are just hurting yourself.

Beachtastic. Your absolutely right, I fell massively for her back then and still have strong feelings for her. I am aware I am being somewhat unrealistic.

The final time we dated, I was paranoid about breaking up, and therefore acted in a way in hindsight calculated to cause a break up. Attention seeking, messaging way too much. I don't think I crossed serious boundaries, but I was not behaving in a mature way

I think she friend zoned you years ago, but quite likes the ego boost of seeing that you still fancy her.

It's not really a friendship. It's you still hoping she might fall for you, but she won't. She's happily single, and career focussed and has made it fairly plain that she doesn't want a romantic relationship with you.

I think she enjoys the companionship with you. She enjoys chatting with you and the attention you give her but I don’t think she has romantic feelings for you.

The suggestion of you staying in the spare room and being worried when you popped up later on one night kinda seems that she doesn’t have the same feelings.

The only way you’ll know for sure is to ask her yourself but I think that fact that you’ve dated a few times previously and it hasn’t worked probably shows that she views you as a close friend.

I have a male friend who I LOVE. He’s great, makes me laugh and all that. He admitted feelings a few years ago, not reciprocated.

You either want a friendship (you don’t) or a relationship (you do). She has been clear, it’s you who’s not. Just stop torturing yourself and slow fade.

Well, only you know the person concerned, OP, and even YOU have no idea how she feels about you, so we can only wildly guess and/or project.

It's quite common to have a "one that got away" feeling about someone from our past. I had it for years, didn't act on it, and am now (many decades on) quite glad I didn't. That's not to say you should do the same - I'm all for "nothing ventured, nothing gained"!

One thing that occurred to me reading your posts is how hard you might be on yourself for not having been more mature in the past. Guess what, we were all wankers in the past! It's part of growing up! Some of us are still wankers, and probably always will be! 😂

There can be a tendency to reflect on past "failures" and want to put them right, which again would artificially elevate her status in your eyes. Think back to university days... the first time we've lived away from home; we were all children, really, finding our feet as best we could.

Perhaps a lighthearted message to her saying how much you enjoyed seeing her again and adding something like "Just checking if I am firmly filed in the friend zone? No problem if so, just managing expectations" and see what she says? If that is enough to put her off seeing you again, she is neither romance material nor a particularly close friend.

You've held a candle for her for so long (and may be relatively inexperienced on the dating side of things since your divorce???) that you might not realise you're in your prime and there are plenty more fish in the sea. Not online dating, but things like smaller independent music festivals where it's easy to chat casually with someone, find common ground (musical taste is a great filter) and then get lost in the crowd if you don't connect.

Whether you end up dating her, seeing her as a friend, or not having her in your life at all, it's all good. We learn and grow from difficult experiences, and part of you must be ready for that after what might have been a fairly static/isolated life abroad.

You might also find that if she does date you, it all turns out nothing like you anticipated. Life is full of surprises!

Good luck 😊

Thanks for the advise. It has clarified things in my mind, which has been helpful.