(Insert gasp here.) “Age is a challenge, and I don’t know why,” Simmons says. Are they broken from former relationships and think that if they go younger they’re going to have better success? When you’ve been married for 30 years, that happens.
I hear that from a lot of men: ‘My wife didn’t want to.’ Whether that was go here, play golf, go boating, travel, whatever.” But while the mystery of why men would be interested in younger women has some perplexed, others, such as the matchmaker L’Heureux, recognize there are still some good ones out there.
Then again, her bar might have been set low when she discovered at least one of her former dates could be found on the website dontdatehimgirl.com, a website that serves as a warning to others. She wants an actual man who plans dates and picks up the phone and brings flowers. “To start a new life after death, divorce, end-of-life parenting—and we’re all searching for that right fit.
“It’s true, Naples is a tough town for singles,” she adds.
“He said, ‘Not really.’ After being pushed, he came back with, ‘Well, Easter Island.’ ‘Well, that’s interesting,’ I said. I never left the airport.’ “It turned out he was only interested in becoming part of the top 5 percent of a frequent flier top-tier program. Just flew from place to place building points,” Ottenstein adds.
“I actually went out with him a total of three times because I thought I was missing something.
In fact, it’s L’Heureux’s job to find her clients just the right match painlessly and without all the drama. For her art, Simmons has had some luck with Selective Search and Millionaire Match.com, another matchmaking service, and though neither connected her with the man of her dreams, they did match her with suitable men she was interested in. “I’m actively dating—but I’m not searching,” Ottenstein says. You’ve got to tell people because a lot of times people don’t know. I’m someone who’s focused and goes for the brass ring.
“They feel like they don’t really need to put any work in,” says Catherine Clarkson*, a 58-year-old divorcée who’s lived in Naples since 2010.
never be another man in my life,” says Paulette Fischer*, a 73-year-old Chicago transplant who now calls Sanibel home. I know I adore Southern men.” But her story isn’t an anomaly.
“Let’s just say the singles scene seems to suck for ladies my age, as we women are 4-to-1 to men,” says Michele Eddy, with a laugh. Maybe I should be matching people geographically first.
“They don’t want to buy someone another house, another car.” “The people they’re meeting are not serious about a relationship,” L’Heureux says.
“There are a lot of players out there that are not serious—are not relationship material.” And then there’s the elephant in the room: Many single men are looking for younger women. From using online sites to being fixed up by friends to even hiring a professional matchmaker, Eddy has gone above and beyond to find what she’s looking for—to no avail.