Frustration After 50: Trying to Find That Dream Date

Group meetings can help navigate the dating scene after age 50. (

Group meetings can help navigate the dating scene after age 50. (

On a recent weekday morning, life coach and psychotherapist Ava Barron-Shasho pointed to the sofa in her cozy Pikesville office.

“I’ve had so many people in my practice sit on that same spot on that same couch and say exactly the same words,” she said. “‘Why can’t I get a date? What’s wrong with me? Am I going to be alone for the rest of my life?’ I knew that if I put  together a group of people who were all trying to navigate the dating scene, they could help one other and see that they weren’t alone.”

That’s how Dream Dating 50+, a bimonthly group for middle-aged men and women trying to navigate the dating scene, started.

Group member, Sherry H., 56, who asked not to use her last name, said one reason she joined Dream Dating was to get some clarity on dating etiquette. Sherry, who is divorced, said she was  uncertain about when it was reasonable to allow a man into her home, and more generally, whether to trust men she meets on the internet. “People aren’t who they say they are,” she said, and noted she tries to “check people out to the best of her ability.”

Sherry finds it comforting to know  she is not the only one dealing with the frustrations of dating over 50.

Steve S., 60, also choosing to remain anonymous, is another group member. He said he’s been dating regularly since his divorce five years ago. Though he has met many women, he hasn’t found anyone exactly right for him.

“Dating at our age is a double-edged sword,” Steve said. “It’s easier because you aren’t looking to have kids together or necessarily to share finances. You just want a companion to enjoy doing things together. On the other hand, at our age, people are set in their ways. Everyone has their own lives.”

Sherry and Steve are both Jewish, though the group is open to people of all faiths. Both say they are not religious, yet both prefer dating others who are Jewish.

“I dated a non-Jewish woman who was really sweet,” Steve said. “But something was missing. … When she started talking about Christmas, I just couldn’t relate.”

“Being Jewish is up there,” said Sherry,  referring to her list of attributes for a  future mate. “It’s not about religion, it’s about culture. Jews have a different sense of humor, you know? I was brought up with a little bit of Yiddish, and this guy I dated looked at me like he didn’t know what I was talking about.”

Sherry believes that the internet has made people unmotivated about leaving their homes to meet others.

“The internet is a blessing and a curse,” she said. “I think people go shopping [on the internet]. They make a date and if something better comes along they cancel. Whatever happened to people fixing you up? No one does that anymore.”

Barron-Shasho said she’s aware that the internet is the main source for dating nowadays. She addresses that in the group.

“One night, someone showed us his dating profile, and the other members gave feedback,” Barron-Shasho said.

“Everyone wants to meet someone on the internet, but I asked them to consider what else they are doing to meet new people. There are so many ways to meet people  if you’re willing to go outside of your comfort zone. A couple of people said they were willing to try that but weren’t willing to do it alone. So two women in the group have gone out to a singles event together.”

That didn’t go so well.

“There was nobody there,” Sherry said. “Here’s the thing. Where do the single Jewish people go? I think the temples should offer singles events.”

During another session the group  discussed whether they were willing to make changes in order to be in a relationship, Barron-Shasho recalled.

The internet is a blessing and  a curse. I think people go  shopping on on the internet. They make a date and if  something better comes along they cancel. Whatever  happened to people fixing you up? No one does  that anymore.” — Sherry H., member,  Dream Dating 50+


“Most people said, ‘I’m at the age where I accept myself. I love myself. I don’t want to change.’ On the other hand, one person said, ‘If you tell me that I’m doing something that is off-putting [to potential dates], I might change that.’”

Barron-Shasho said people in the group run the gamut from those who date constantly but don’t meet anyone who’s right for them to people who don’t have dates because perhaps they’re more selective or are ruling people out too quickly.

“Sometimes people will see someone online and ask themselves, ‘Do I like his looks?’ That will determine whether they contact him,” Barron-Shasho said. “I suggest that people look at other qualities as well as looks, and I also recommend that they date a person more than once. Relationships aren’t like instant mashed  potatoes, I say. They’re not just ‘add water and mix.’”

Since Dream Dating is a coed group, men and women are able to share their perspectives with one another, helping each other to interpret the sometimes mysterious behaviors of the opposite sex.

“One woman in the group was talking about how she wanted a man to treat her when they were dating. She wanted daily texts,” Barron-Shasho said. “Well, a man in the group said, ‘No. If you’re expecting a text every day, that’s too much work for a man.’ It helped her to get a man’s perspective.”

“One time we talked about flirting, Barron-Shasho said. “I asked them, ‘What’s a good line?’ A man in the group said, ‘Compliment me on something I’m wearing. Nice tie, nice shirt. That’s all you have to do.’”

As group leader, Barron-Shasho, who has 20 years of experience, said she brings a positive and hopeful outlook to the sessions.

“Just because it hasn’t happened yet, doesn’t mean it’s not going to,” she said. “And

for now, Steve and Sherry are both pleased that they are each being fixed up with a friend of the other. Let’s see how that goes.”

Dream Dating 50+ is accepting new members. For more information, visit

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