Drop this idea altogether or "do" something.
I have a friend. Not especially close, but I've known him for a decade or more.
For most of that time I was married, I haven't been for 2 years now.
He is divorced and has had numerous girlfriends during that time. All much younger than him and very attractive. Usually last a year or so. Lots of female friends too. AFAIK he's never had more than one GF at a time but he does move on fairly quickly and he always seems to have women (often married) around him.
However, he split with the last girlfriend around the same time I became single. He told me then that he planned to stay single for a while and he has. During that time he's become a good friend to me. Has been there to help in practical situations and been important socially, as my life and friends changed completely after DH's death. We shared one very drunken kiss which we have both pretended never happened, but apart from that he's always been respectful and never tried anything on. (I'm also not sure who initiated the kiss!)
I don't think he's a player. I think the string of women is because he's looking for love, but looking in the wrong places (young attractive women!).
It has occurred to me that the reason he's been single for so long, concurrently with me may be that's he's a carrying a torch for me, although I'm well outside his usual target market.
Anyway, if there is "something" I think he's waiting for some sort of sign from me that I'm ready to move on/when it would be acceptable. I've no idea what the answer to that is. I wouldn't object to a bit of fun, but I'm definitely not looking for "the one" as I suspect he is. I'm also worried that moving things on with him ruins the friendship, but also know that would have to change should he (or I) have a partner anyway.
Or he could not be interested but grateful for a friend in the same way I have been.
What do you think?