In fact, talk to virtually any single woman over 40 in Southwest Florida and you’ll hear a similar story: multiple women for every man, unresponsive online matches, a shallow dating pool, and, of the relatively few dateable men around, poor manners and an understanding they are a hot commodity.
“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.
(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.
The same can be said for Stephanie Rogers*, a 50-year-old philanthropist who’s been divorced for several years and struggles to find local men of any caliber who hold her interest. So the truth is we don’t really know just how many single men there really are in Southwest Florida—could be hundreds of thousands or, as Clarkson says, “there are 15.” But even if the lack of actual single men isn’t a problem, the lack of “qualified” men certainly is.
Let’s face it: Many single women in this area are in a financially secure place; they’ve either made money on their own, been left it by a deceased spouse, or married well and divorced better.
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.
“I do encourage women to get involved with some of these more upscale dating services,” Simmons says. A lot of times people will assume that I’m too busy, but I’d love to meet that special someone.” But not just anybody. But I think a lot of men in Southwest Florida don’t know what they want. I think Southwest Florida has become a place where people come to heal,” Ottenstein says.
“I asked him if he went anywhere interesting,” Ottenstein says.
“He said he came straight from fishing because he lost track of the time,” Clarkson says. Marla Ottenstein (pictured), owner of Professional Organizer Florida and the writer of the , met a man who appeared to check off every requirement on her list of wants.
“He smelled like bait, then took me to a seafood restaurant. He was tall, handsome, smart, well-off, well-dressed, well-read and well-traveled.
(But) I’ve been alone for a few years now and it seems harder than ever to meet a man. ” This may come as a shock, but being a single woman looking for love in Southwest Florida poses some challenges. “(Perhaps) my prince is riding his white horse somewhere else?
“I’m thinking I’m either hard to match—wonderful as I am—or this is a geographically undesirable area for me,” says Eddy, who splits her time between homes in Fort Myers and the Panhandle.