Separated from husband year and a half ago. Amicable and we are both happier on our own. I am 50.
I don’t want a relationship and I am very happy on my own, financially independent, etc. However, I would like to have a bit of company, friends with benefits kind of thing.
I have decided not to do OLD as I don’t think I could cope with the rejection and ghosting. I would like company and sex (before I die...) but with someone I trust and like.
I recently heard about an old two night stand who is getting divorced and I have been thinking of getting in touch but I have not seen him for about 20 years. Our short fling was great but there was no indication of any interest from either of us, it was a crazy time, so it did not go anywhere. I felt we had huge chemistry and I really liked him and I would definitely go there again.
I know a relationship would probably not work as I would not fit into his world (sporty, well established social group). But I absolutely do not want that. I think we could just have some fun on a casual friendly basis. I have tried to engineer a meet-up with mutual friends for the last year but have been very subtle and then time lockdown hit so I could not pursue that.
My dilemma is whether to FB friend request him. We have about 20 mutual friends so I don’t think it would be too stalkerish (but maybe a bit) and I see 3 or 4 of them a few times a year, but it would be a very obvious message that I am interested. I know it is easy to say go for it what have you got to lose, but I am not sure I could cope with the humiliation of rejection. And what if he is horrified? He was a bit edgy and very popular in his social group so I am very nervous about initiating anything in case he and his friends all have a good laugh. They know who I am but I have never been one of their group so not seen any of them for 20 years or so.
What do men think about these things? What do you think should I do? I feel a bit pathetic asking but I have never made the first move and I feel it may put him right off.