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Ready to Start Online Dating After 50? Be Prepared to Meet These Guys, But Would You Date Them?

By Shirley Goldberg April 06, 2019 Dating

A friend of mine in her early 60s was surprised when a man she met for the first time for a coffee date asked if she’d like to get together for dinner the following Saturday.

“Why would he want to see me again?” she said.

“Why not?” I said. “You’re cute and fun to be with, so why do you ask?”

“I know everything about him. He was a police detective in New Jersey, he’s got three grandchildren, and he likes trying out new recipes. On the other hand, he didn’t ask me one single question. He knows nothing about me. What’s with that?”

Should Talky Guy Date Himself?

My friend had met Talky Guy, one of the guys you’ll probably meet (or have already met) when online dating. She didn’t think he was keen on her because he took no interest in her during their meet. Or so she thought.

“He showed interest by asking you out again,” I pointed out. I suggested she give him another chance, that he may have been nervous, especially if he was new to dating.

My very own Mr. Talky told me a wordy date-from-hell story, followed by a long anecdote about his last meet, a bust. “So,” he said, finally coming up for air, “do you have any dating stories?”

A Lot of Blah Blah Blah

Even though I think it’s tacky to discuss other online dates on a first meet, I made a stab at it. Here’s how the conversation went:

Me: Well, yes. One man I met didn’t even come into the restaurant. He stood outside staring––

He: Oh, I had a woman stalker I went out with three times––

Me: And pointing at himself and at me—

He: Luckily, she didn’t know where I lived. Then this other lady decided she really liked me and kept texting. Twenty texts a day. She… blah blah blah blah…

Me: Oh, and did you––

He: The worst was a friend who put the moves on me. She leaned over the table and bla bla bla bla…

Yes, an overly talkative guy may be nervous. Or he may be in love with the sound of his own voice. Or maybe he spends most days alone without adult company. Whatever his excuse, he could be worth another date to find out if there is more there than extreme self-interest.

My friend, who met the former New Jersey police detective, went out with him again, and said he was more relaxed, asked her two questions, and complimented her on a necklace she was wearing. They’re going on a third date.

Should You Trust Unreliable Guy?

If you’re online dating, you’ll probably meet Unreliable Guy. Of course, you can’t tell he’s unreliable, not right away.

My unreliable guy was Dougie, and I was a newbie at online dating. (Yes, he called himself Dougie, not Doug.)

Although we planned our first meet on the phone, it was difficult for him to pin down a time because of his job. “Sometimes my boss sends me out at the last minute,” he warned me.

The evening we were to meet, he was indeed sent out on a call at the last minute by his boss. (He was foggy about his job description, and since I hadn’t even met him, I didn’t ask too many questions.) At 10 p.m. he called and apologized.

He emailed me again a few weeks later, then telephoned. “Sorry it’s been a while since I called. But, hey, we’re both still on this dating site,” he said. He had a point. We set a date and time on the weekend, when he didn’t work.

I was going out of town, but I’d be back Saturday morning, the day of our date.

“Call me,” he said, and when I got back, I did. It went to voicemail, and he didn’t call back. I wasn’t angry; I was almost amused.

And I hadn’t put on makeup or changed, pretty sure a guy who is unreliable once will prove himself unreliable always.

Nowadays, one cancellation is all I allow.

The Unreliables really should find one another and date. Save the rest of us the trouble.

Shouldn’t Not-Really-Separated Guy Be Honest?

Phillip turned up about 10 minutes late at the restaurant, but he apologized sweetly and sat down, asked about my day, and ordered wine. Once the waiter brought our cabernet, Philip raised his glass in a toast to our meeting. I glanced at his hand.

He was wearing a wedding ring.

Phillip had listed himself on the dating site as SEPARATED. To me, this meant legally separated. He’d told me on the phone his wife was in long-term care with rheumatoid arthritis. I didn’t probe then, thinking I could ask questions when we met, if necessary.

Since the ring was out there in plain sight, I asked about it. I was irritated, and I didn’t hide it. “Are you legally separated?”

“I told you about that,” he said. “It’s pretty clear. We’re as separated as anyone can be separated.”

I asked a follow-up question: “Do you live with your wife?”

“My wife is living at home. My son is taking care of her tonight so I could come out. She’s gone downhill, had a leg amputated.”

A horror story, and I wondered about their connection, thinking, you’ve got to be close to be so supportive.

“You told me long-term care, of course,” I said. “But if you’re living together, you’re not available.”

Philip ordered a fourth glass of wine, much to my and the waiter’s surprise, but I didn’t stay to keep him company.

Mostly, I felt sorry for Philip and his wife. A difficult situation for them both, but even so, he hadn’t been honest with me.

A deal breaker.

Dating a separated guy who’s on his own is one thing, but even so, it’s best to tread slowly around any man in transition. A man who is separating needs time to think about what contributed to the crumbling relationship.

After meeting Philip, I stopped even considering “separated” guys because I felt they needed time on their own to work through their issues.

Should You Date Clueless Guy?

Clueless guys are priceless, at least compared to many others you’ll meet online. They mean well, and they can be trained. Often, they are new to online dating.

Clueless guys don’t know they should be specific when they ask you to meet. They’re not sure how to arrange a meet, and they’re not sure if they should ask you out for coffee, a glass of wine, or dinner.

A clueless guy can come off as socially inept because he’s out of practice. Clueless guys tend not to know how to dress (those white sneakers have to go), and sometimes turn into Mr. Talkys out of nervousness.

Often, a guy who’s clueless has been inside his little cocoon of safety, secure in his post-divorce (or widower) routine. Someone or something shakes him up, though. And he decides he needs more in his life, so he starts to date.

The clueless guy, a friend of mine, is dating was lucky enough to have an ex-wife who prodded him to start online dating.

Would You Date Them?

These “types” I’ve described are meant as guidelines. If nothing else, they’ll remind you that you are not alone, that online dating can be rewarding, yes, and at the same time, frustrating.

What experiences have you had in the online dating world? Did you find yourself jockeying to say a few words on a first meet? How did you handle it? Share your thoughts here, and I will respond.

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The Author

Shirley Goldberg is the author of Middle Ageish and Eat Your Heart Out, both romantic women’s fiction with seasoned characters. Her website,, offers a humorous look at living single and dating in mid life. Shirley’s friends nag her to tell them which stories are true in her novels.

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