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Ahead of the Curve: In Hot Pursuit

Where to find the date of your dreams

Adam McCauley


When it comes to meeting singles in Southwest Florida, you have three options. You can do the online thing. Of course, that requires trying to figure out whether a guy’s description of his being a “lady killer” is literal or not. (Hint: don’t date him either way.)

Alternatively, you can leave yourself in the mercy of the smug marrieds, who inevitably coo about knowing “just the perfect person to set you up with.”

Or you can try to find other singles as they roam their native habitat. But it’s a jungle out there, and, to survive, you’re going to need a guide, or at least a map. So we’ve drawn you one. Happy travels.

Looking for: Singles who don’t balk at $16 cocktails

Head to Truluck’s. While this tends
to draw an older crowd, you can find younger working types at the bar, too— especially during the nightly happy hour when practically everything you could want is on display. “People love our happy hour. There’s often a line out the door,” says general manager Tim Irving.

Looking for: A casual guy who loves your sports team

Don’t leave meeting someone who also loves Ohio State University as much
as you do up to chance. (Or worse,
risk falling for a Michigan fan!) Head straight to Harold’s Place, where the game is always on.

Oh, you’re a Chicago Bears fan? Head to The Edison—which hosts the Southwest Florida fan club each Sunday. If you love all things Iowa Hawkeyes, you’ll find your mate waiting for you at Ron Dao’s, and if it’s a Beantown babe you’re searching for, head to Foxboro Sports Tavern.

Looking for: Someone for now (preferably in a mini-skirt)

Blue Martini is probably about the closest thing Naples has to a big city-style dance club. Expect thumping bass, dark corners and DJs spinning big radio hits. The rumor here is that the older men and younger women rule the early hours, and then—between 9 and 11 p.m.—the demographics shift and older women and younger men party late into the night.

In Fort Myers, folks flock to The Firestone’s Sky Bar for the bottle ser- vice and DJ treatment. One floor below, the martini lounge offers similar VIP treatment with a slightly more relaxed feel. Perfect for chatting up that person you just met on the dance floor.

Looking for: Someone active

Gulf Coast Runners has been organizing races for several decades, but its secondary function has really been serving as a venue for active singles to meet. “GCR has had a lot of new romances that were spawned by our group runs, races and social events,” says Mitch Norgart, executive director for the group. The group’s Dash and Dine events (three-mile runs followed by snacks and mingling) and Bagel Runs are particularly good for mixing with other single runners. 

#2: The ranking that dating website ourtime.com gave to Naples for best place to be a single mom age 50 or older


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