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Now they’re at a place in their lives where they recognize they need a man who can keep up with them—both emotionally and financially.For some, if guys don’t have the wherewithal, there’s a serious hesitation to even bother. “Some of these men have split their fortunes—sometimes multiple times,” Simmons says with an understanding tone.

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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. 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. Having been widowed more than 10 years ago, Eddy has begun to be proactive in looking for a significant other.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.

They were enjoying a lovely first date, finished dinner and decided to keep the night going with drinks at a nearby bar.

Within minutes another woman came up to her date to say “hi” and introduced herself to Schantz.

“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.

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.