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I M35, have feelings for my oldest friend, F35, and I think they might be reciprocated, how do I proceed?
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I (M35) have known "Katy" (F35) for my entire life, our dads were at school together.

For all that time we have been close friends, especially in the last few years, we have travelled together several times and see each other every couple of months at least, talking on the phone fairly regularly.

In the past I have had quite strong feelings for her, frankly it's hard not too. She is intelligent, funny, kind and anxious in pretty much the same way as me, shares pretty much all of my values and also happens to be fantastically beautiful.

I took those feelings an put them to one side a long time ago, content to be her friend and accepting nothing was going to happen. That state of affairs was fine, I found someone else and was in a relationship for 13 years

She had a succession of unsuccessful relationships, mostly with useless posh boys who never really got her and generally buggered off when they realised she still has issues from family induced trauma.

About a year ago me and my ex split up, long story, messed me up for a while, but I'm getting to the point I'm ready to try again.

I recently went on holiday with my sister, who is very close to both of us, and she said she thinks me and Katy would work well together. My sister told me that the way Katy talks about me suggests its possible she has feelings for me. Notably katy said nobody has ever made her laugh the way I do.

That opened a real Pandora's box and all the feelings I had put aside came rushing back. I realised that if she reciprocated I could happily spend the rest of my life with her.

And here in lies the issue, Katy's friendship is probably one of the most valuable things in my life, and I care far too much about her to want to risk upsetting her. I'm keenly aware of how devastating it can be for a long term friend to confess unrequited feelings, though I hope I wouldn't be so basic of falling into the pathetic and gross anger men can show on rejection.

I have no idea what to do now, if there's any mutually to the feelings this could be the best thing to have happened in both our lives, but the risk is pretty high.

I am committed to taking no for an answer, I can live with that, but even asking could change everything.

Any insight and advice appreciated!

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1 year ago