Dr. Bill, I'm a man in my late forties and about a year ago I dated a man who was somewhat younger than me -- all right, a lot younger than me -- and he seemed to really be into me. Because of the age difference and because he was so attractive, I hung back a little and sort of let him do the pursuing. I guess I couldn't quite believe that he was really that interested in me or I was just afraid I would be seen as the desperate older man stalking the younger guy or something like that. In any case, I took my time responding to texts and phone messages and eventually I stopped hearing from him. I always hoped that we would run into each other again, but I checked out his facebook page and now he has a lover -- closer to his own age, of course. I'm happy for him , of course, but I'm left with the feeling that had I only not hung back, pursued him more ardently, I might be his lover today. I'm not even certain what I'm asking. I haven't checked out his facebook page since and I won't but I find myself thinking about him a lot. I wouldn't quite call what I feel heartache, but nonetheless it hurts. What do you think and what can I do to make this feeling of regret and loneliness go away? I don't think anyone like him will ever come my way again.
Get out of the house, join gay dating sites if you haven't already and follow up on interested parties, hit a bar that caters to men your age or mixed ages, call up some friends, have drinks or dinner and exchange war stories, commiserating over romantic misfires. Stay away from friends in happy relationships for awhile as they may only remind you of what you're missing. Have some hot consolation sex. Or hot chocolate if the former isn't available.
I have been in a similar situation, and you'll never know if the guy stopped calling you because you didn't pursue him enough, or because he just wasn't that into you when all is said and done, or if he, frankly, ultimately wanted a man in his own age group. You may never know, so forget it. Stay off his Facebook page -- you don't need to see photos of him and his lover enjoying happy domesticity. Or getting married! Believe me, you really don't need that torture.
You say that you don't think anyone like him will ever come your way again. First, you can't really know that for certain. Second, the next man you fall for [and who will hopefully fall for you] may not be as young and handsome as this guy, but he will still be "Mr. Right" if it turns out he's The Guy. You're certainly not too old to find a long-lasting relationship. [I mean I know men in their seventies who have fuck-buddies, sometimes much younger, or who have found soul-mates in their senior years -- you never know!]
Do not think of this guy as your last chance. There's always somebody interesting around the corner, you just gotta get out there and meet him. Take it from one who's been there: after awhile you won't even remember what this guy looked like [admittedly it might take a little longer than with other guys].