Dating After 50: Let’s Tell People We Met in a Bar

A couple dating over 50, kissing on the beach at sunset.

The use of online dating is exploding, but for some, especially those over 50, it still has a stigma. As one online meme puts it: “Join an online dating service? I’d rather meet someone the old-fashioned way—with alcohol and poor judgment.” One night I had the opportunity to see if a more traditional pick-up method worked any better.

My girlfriend Debi and I (the fearless duo) were at a local restaurant for happy hour and as it so happened, she noticed a guy at the other end of the bar, drinking alone and alternately watching the college basketball finals and looking at her.

She said, “He’s looking again. Check him out. I think he’s cute but I can’t really see him (she needs glasses but refuses to get a prescription—more of that aging denial stuff).

I snuck an inconspicuous glance and gave her my approval. “Oh yeah.”

“I think he might be too young though.”

“Nope. He looks your age. And he’s cute.” (No matter how old women are, we still call men we’re attracted to cute.)

“He keeps looking down here.”

“You think he’ll come over?”

“I have no idea.”

We finished our drinks and paid our bill. The guy at the end of the bar never came over. As we were about to leave, Debi asked the bartender for a pen and jotted something down on a cocktail napkin.

“What are you doing?”

Instead of answering me, she leaned over to the bartender.

“Would you mind giving this note to the guy down there at the end of the bar when I leave?”

The bartender was nonplussed. “Sure, I’d love to play matchmaker for you.” And with that we sauntered out, headed toward our cars.

“Oh my God! I can’t believe you just did that!”

“I’ll probably never hear from him.”

The next day she got a text.

“I’m the guy at the end of the bar from last night. Yes, I’m single and yes, I’m interested.”

They texted back and forth. He invited her for a glass of wine. Teeny red flag—the invitation was for 7:00 p.m. but specifically did not include any mention of food. Just a glass of wine. Kind of a weird time to pick, we thought. No biggie. There would probably be appetizers, once they got there.

He was still cute when she saw him up close—a relief. He talked about his business as a tennis instructor. Never married (red flag). No kids (red flag). Over to her. My friend’s life is full, kids and grandkids, a variety of different jobs and businesses; her stories are many and her personality is distinctly bubbly. She noticed he yawned at one point.

By 7:45, there was no mention of food. By 8:00, the glasses were drained and my friend was starving. No conversation about seeing one another again. No chemistry. One and done.

So while online dating may seem a less romantic or “natural” way to meet someone, it’s a major time-saver. You waste less time on dates that go nowhere and you can catch a lot of red flags by reading profiles first.

Just like the book, “Secrets of Dating After Fifty,”  says—all you know about someone when you meet them in a bar is that they’re cute and they drink alcohol.


Karen Haddigan is the author of the recently-released book Secrets of Dating After Fifty: The Insider’s Guide to Finding Love Again.

Karen Haddigan


Karen Haddigan is the author (in collaboration with Debi Helm) of the upcoming book Secrets of Dating After Fifty: The Insider’s Guide to Finding Love Again. She met her ex-husband online and after her divorce several years ago, re-entered the world of online dating. She has a background in mediation, communication skills, and conflict resolution.

Learn more about Karen and dating after fifty at

No Comments Yet

Comments are closed