How do let him know I'm interested?

[LadyMaine]

I'm sixty and have been single for five years. After some lacklustre online dating I decided to remain single.

Last summer an old friend who lives abroad and his (grown up) daughter came to stay for a lovely few days. We lost touch when he moved abroad a decade ago and it was lovely to reconnect.

He recently told me that he is now divorced from his wife of 30 years. In the last month we've spoken every week and I haven't laughed so much in years.

I think there might be something between us but I did previously tell him that I was sworn off men. He's a perfect gentleman so I don't think he is going to initiate anything.

He's coming to the UK again in September and will spend a few days with me. How do I let him know that I am now interested in him romantically without ruining a forty year friendship if he doesn't reciprocate?

PS. And should I say something before the visit or wait until he's here?

It's possible to just enjoy his company and laugh like you did. You don't have to do anything because it seems like things are already progressing well.

Also observe how he behaves and what he says. Could he be attracted to you romantically as well?

Before you decide, do you think he would want to come back to the UK to live? If not a long distance relationship could prove difficult to sustain. If it's a possibility then carry on having fun together when he visits and perhaps before he arrives you could let him know how much you've enjoyed chatting and can't wait to see him again.
You could say that he's made you change your mind about giving up on men! Then the ball's in his court.

Great suggestion to let him know that he's restored my faith in men. I don't know whether he is considering moving back, his job involves a lot of travel. Long distance wouldn't be a problem for me as I don't want to live with anyone again.

You're right, things are progressing well, part of me thinks it's all too good to be true. I also feel a little guilty about his (ex)wife as I really liked her (but I knew him well before they met.)

If he's not interested in me romantically I don't want it to affect our friendship. But I think I'd be crushed by rejection because, given what I said to him before about not being interested in men, I'm going to have to make the first move.

With the benefit of hindsight, I think he was sounding me out before he told me he was divorced.

I think you have to decide if you are robust enough to be able to cope with him saying he only sees you as a friend and not in a romantic light. But if you don't give him a hint as to your feelings you will never know as up to now he thinks you are not interested in a relationship. Also why did his marriage end? Do you know for certain he hasn't met someone else?

It depends whether you could cope with the rejection. Personally, it would spoil a friendship for me if that happened - there'd always be a faint aura of humiliation however well he handled it, and then the possibility of having to say all the right things if he met someone else.

I would de-personalise your 'statement of availability' as much as possible - perhaps just say you're over your sworn singledom now and thinking of getting back into the dating scene.

You've also got to consider whether there would be a future for you as you live in different countries - would either of you be prepared to move? Otherwise you'd be looking at a long-distance relationship and I don't think there would be any point in tying yourself in this way for the sake of occasional visits - you might as well remain good friends.

I'm definitely going to need an update on this when you tell him. I love this kind of love story 🥰

How are things, OP? Any news?