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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.“They don’t call when they say they will, they don’t plan ahead when you actually do get a date, and they don’t seem to own a real shirt anymore.Apparently you move to Florida and all you can have in your closet is T-shirts and polos.” She actually had one suitor show up to their first date 20 minutes late wearing a filthy Hooter’s shirt. ” Things could have been worse: He could have seemed perfect from the start.In fact, during their first date he mentioned he had traveled around the world four times just that year.“I asked him if he went anywhere interesting,” Ottenstein says.“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.

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She met a charming, good-looking man at a speed-dating event.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.The man got a bit awkward but kept the date going, but the woman never left them.“It turns out he had met—and slept with—this other woman the night before,” Schantz says.

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