Dating Tips for the 50+ Crowd

Those of us starting over for the second or third (or fourth) time have a billion dating questions that go beyond, "What now?"

By Jackie Dishner

"Whatever you do, don't sleep with him on the first date."

No, that's not what my mother told me in high school. That's what one of my editors told me over lunch after my third marriage ended.

"Wait six dates or six weeks, whichever comes first," she told me, sipping her pinot gris. "Then, you can sleep with him."

Great, I thought, something else to count besides days till the next mortgage payment. But, wait! She even told me how to find that first date – on the dance floor at a country bar.

I didn't bother telling her I can't dance, let alone two-step. Ugh!

Those of us starting over for the second or third – or fourth – time have a billion questions that go beyond, "What now?" And we may not yet be ready for Harlan Coban's new dating manifesto, Getting Naked: Five Steps to Finding the Love of Your Life, despite its subtitle, "While Fully Clothed and Totally Sober."

But it doesn't hurt to be hopeful. With online dating, speed dating, couples dating, and a whole maze of other choices, surely we can get this right. After all, Gian Gonzaga, senior director of research at, once told a reporter at Time magazine about the 50+ crowd, "Once you shove them out there, they adapt quickly."

I can attest to that, but…what now? A few tips from someone who's been there, done that:

Sex Can Wait
Don't sleep with them on the first date? No problem. When you're out of practice, it makes sense to save the good stuff for last – or six weeks, or whenever you find the Viagra. But anyone who shows up at your door flashing a pack of pills should not be let in. Period. “Don’t make sex the objective,” says Tina B. Tessina, Ph. D., L.M.F.T., (aka "Dr. Romance"), psychotherapist and author of The Unofficial Guide to Dating Again (Wiley), “If and when sex is right, it will happen – there’s no advantage in rushing."

Be Open to Opportunity
If you meet your prospect at a friend's party, the two of you get along, and then you wind up leaving at the same time, pay attention to which way he points his car. If it trails behind you on the freeway, it might mean he lives in your neighborhood. Trust me, that could be convenient for future meet-ups – as long as he's not stalking. Plus, it makes it easier to plan your eventual overnights.

You Better Shop Around
Tessina, who is California-based and has authored more than a dozen other books on dating, marriage, and parenting, says to take advantage of the new freedom we have in the second half of life by dating a lot: "You don't have to stay focused on one person until you've given yourself a choice." She says to let character determine how far the relationship goes.

Watch for the Cues
Research about loneliness shows that similarity in attitudes, values, interests, and activities help provide the foundation for future relationships. Your goal is to discover mutual compatibility. So if you are one of the trendy types, meeting your dates online, Tessina says you might get a better outcome if you make sure your first in-person meeting involves doing something you enjoy. If the date doesn't, actions will speak louder than words.

Do you agree or disagree? We'd love to hear your side of the story.


I'm pretty sure the man in the photo accompanying this article is giving a rose to his 30 year old daughter! [o:r as in the case of my 63 year old ex; his 34 year old girlfriend.] Not inspiring.

mizcaliflower on 2012-10-23 12:17:34

Useful information, thanks. We should be careful when dating at our age. A friend of mine Recently found her love on I hope it can help more singles over 50. Thanks.

coolkevin on 2012-10-15 00:01:33

Hey, Jackie, nice piece! I also liked the Dating After Divorce segment. Just signed up for the site, good stuff here. Thanks for sharing.

peglaree on 2012-10-03 14:51:12

I was just thinking last night how freeing it is to never be observed by a member of the opposite sex in the privacy of my home cause I can look and act pretty wild and crazy when I'm on my own -- which at this point is a lot of fun for me.

judyanna on 2012-10-03 13:02:22