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Striking out in the online dating world

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By Laura Stassi
Posted on May 07, 2026

Q: I am 66 and have been divorced since 2019. I’m a semi-retired IT consultant and financially secure. I work out seriously almost every day.

I’ve tried Match, Bumble, Tinder and Facebook Dating — and I’m coming across a lot of fake profiles. This is exhausting. If I do meet ladies, I try to please them by buying them meals. But not anymore. Now I’m just sticking with coffee and keeping it simple.

I try to be nice in any way I can because I want a long-term relationship that will last the rest of my life. But I really think these women would rather be alone with their cats and dogs. Or there’s something going on that’s preventing them from wanting to commit to any possible relationship.

So my suggestion to these women is to relax and trust men. Your thoughts?

—Ray, Maryland

A: I appreciate you sharing what clearly has been a frustrating romance journey. You’re financially secure, you take care of yourself with exercise, you’ve tried multiple dating sites, and yet your efforts haven’t yielded a long-term relationship.

Does it help to know you’re not the only one? According to a Pew Research Center study, 46% of all Americans who’ve used a dating site or app report having somewhat negative or very negative experiences.

Moreover, you’re encountering fake profiles. It surely is exhausting and, unfortunately, common. Older daters, especially those with significant retirement savings, may be primary fraud targets, according to a report by the National Council on Aging. It cited FBI statistics showing that in 2023, daters over 60 years old lost a whopping $367 million in these so-called “sweetheart scams.” It sounds like you have your radar up for potential scammers, which is a good practice.

Another positive? Ditching dinner dates for coffee meetups. I get the impression you’ve changed course because expensive wining and dining wasn’t getting you anywhere.

But there are many good reasons to choose a lower-stakes date situation aside from cost. Personally, I find it difficult to have a satisfying conversation in a restaurant, especially when we wind up shouting to be heard above the ambient noise. (Fact: On a recent first date, I had to lean in so far to hear my companion describe his Christmastime cruise with his daughter that I wound up with tomato sauce on the front of my blouse.)

Also, inactivity such as sitting at a table and eating isn’t necessarily conducive to catching feelings. Have you thought about grabbing a coffee together and then going for a walk in a nearby park, or meeting up at a museum or art gallery for the latest exhibit and then talking about it afterward?

You say you’re “trying to be nice” in any way you can, Ray, and here’s where some red flags start to pop up for me. Is it possible that you’re not being yourself? Not that your true self isn’t nice — but your efforts might be coming across as insincere or stilted.

Or maybe you’re giving off vibes that you’re narrowly focused on finding “the one” when first dates are simply chances to make an interpersonal connection.

In the Dating While Gray podcast episode “Chatting Up Strangers,” marketing entrepreneur Fred Joyal described his winning conversation strategy: Offer a sincere compliment or observation, ask a question, listen to the answer, “and then say the three magic words: ‘Tell me more.’”

“That’s your driving motivation,” Fred explained. “Tell me more — not, ‘I want to tell you about me.’ They will [become] interested in you because you’re so interested in them.”

As for your comment about women preferring their cats and dogs over you … well, perhaps they do. Numerous studies have shown that pets have a positive impact on their owners’ mental health by helping reduce stress and anxiety and offering companionship, among other factors.

But love for their pets doesn’t mean they need to “relax and trust men.” It means, to quote a catchphrase, they’re just not that into you.

I’m sorry, Ray. Sometimes two people simply don’t click, and there’s no point in attempting to analyze why. It’s better to simply move on.

I understand how disappointing and anxiety-provoking it is when the line of people who just aren’t that into us grows longer and longer. But the sooner we let go of the notion we can “fix” these people, the sooner we’ll have more opportunities for connection while, in the meantime, living full and satisfying solo lives.

Laura Stassi is host of the podcast Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships and author of Romance Redux: Finding Love in Your Later Years. Send your questions to Laura at newloveafter50@gmail.com.

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