As to the 39 year old.... why not? Did you enjoy his company? I'm not saying you have to marry the guy, but if you enjoy his company, then go enjoy his company! Stop worrying about the age difference. Sure, you might find you don't have much to talk about, but maybe you do, or you just have to work a little harder to find them. Or even find you don't want to talk to them at all, but still enjoy their company....
I think that's the issue with men dating younger women. We are not focusing on the age difference.
M:23 T:26 Me:53, Wife: 60 S:18 D:16 filed 7/16 W moved out 4/28/17