Tag Archives: cougars

Ask Johanna: Dating After 50

Dear Johanna, 

I’m a 51-year-old woman who has not dated for at least 10 years, since I’ve been so busy raising my son (I’m a single mom).  He’s now heading off to college, and I’m wondering how to go about getting back into the dating scene.  I’m feeling pretty out-of-it, since I haven’t done anything like this in so long.  Any suggestions?

Rusty in Roxbury


Dear Rusty,

I’d say it depends on what you are looking for.  If you just want to go out and have a few good meals paid for by someone else and you don’t care if what you end up with in the bargain is a guy who 1) plagues you for advice on how to win back his ex-wife or 2) talks all night about all of  his unsuccessful investment schemes (“But this one is going to work. I can feel it.”) or 3) describes how great his mother’s bread pudding is, down to the last raisin-filled bite,  which, by the way, he polished off at the house he shares with his mother before coming to take you out, then I’d say try Match.com.  If nothing else, you can end up with some doozies to entertain girlfriends with over coffee.  But if you are really interested in meeting an interesting man, do what my friend, Sadhvi, says and go do things you enjoy doing: volunteer in a political campaign, learn to ballroom dance, attend lectures at your local university.  If the activity is interesting, at least you won’t feel like you’ve wasted an evening. But I don’t know about her bowling suggestion, since I’ve never been too crazy about the guys who hang out in bowling alleys.  Maybe the best idea would be to hang out in the lobby at a therapist’s office, since a lot of men over 50 are probably inside on the couch. Continue reading Ask Johanna: Dating After 50