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Dating: A Guy’s Perspective

Funny anecdotes on dating in Fairfield County.

Photograph: ©-RapidEye/istockphoto.com

I have dated extensively in Fairfield County. It’s a mixed bag. A bag you can’t escape sometimes! For the single guys out there, I’ve got some observations to share as well as some Do’s & Don’ts…

Why BarTaco’s A Bad First Date

Major Reason: You will NEVER hear a word your date says there. Ever. You won’t even hear yourself think; with music that loud you might be deaf by the second drink. And gingham’s fine, but, there’s a limit.

Don’t Go To Brooklyn…

Why? I’ve clocked it. Two hours: Park car (steep fee); Metro-North ticket/MetroCard; ride down, subway change at Grand Central, switch at Atlantic Avenue, then, maybe, another change. Know where else you can go in two hours, in a fast car? Massachusetts. Makes you think.

Check Papers…

Divorce is not uncommon in Fairfield County dating. However, separation means marriage, not divorce. To some, “I’m single” = “I’m interested.” Legally, that’s still marriage: A husband could be out for vengeance once he realizes you’re out with his estranged wife. So really, the divorce certificate is the key…just sayin’.

Stamford’s Perviest Road (Ahem, Franklin Street)

You’re at a downtown bar late, can’t drive home yet, but you’d like to share a moment, and parked on this boulevard in The City That Works. It was utterly deserted—but, once you embrace, pervy people magically appear, peering into your car, voila! urban gawking.

Why It REALLY Should Be Named OKStupid…

Think about it—online dating profiles require a pound, not a pinch, of salt. It’s the Internet: trust NOTHING! So, OK, Cupid: My Quiver’s full! But that cute, perfect lady from “Rowayton” you spent a month on? Well, shucks. Turns out she’s a Clevelander and just interested in saying hi to someone from the Gold Coast. Go figure.

From Azerbaijan With Lust

Language barriers can be alluring, but if you met at Chocopologie, and all you have in common is coffee and physical interest with those emoticon-filled, six-hour text dates, then: You. Are. Doomed. That’s not love: that’s lust. You should know better.

Small Dogs Are A Fashionista’s Best BF…

Dating someone in the runway biz? Good luck, because you’re dating her and her dog in the FC. Trust me, first you’re nuzzling a lovely lady, next thing, a Chiwinnie rescue named Chanel is nuzzling you as you’re carrying her in your consort’s Fendi Selleria. It happens, and it’s not glamorous.

The (Socialite &) Boozy Chef

Haute Cuisine can be a synonym for “80 Proof” around here. Sorry: It’s bad dating women who ambled in the upper echelons of the social scene and found their true calling, after a decade, through a love of professional cooking—and fine wine, fine scotch, fine brandy, and finer spirits, enjoyed excessively. And, if there’s a small dog involved, too—run. Fast.

Do’s & Don’ts

Don’t expect to find a dream woman immediately. It takes a while to reel in a dishy catch, even in the dreamland of, say, Greenwich. (Psst: And don’t think the above “types” are “typical”…and, um, “dream woman” doesn’t always mean it’ll work out.)

Do enjoy the dating merry-go-round, because at least you’re getting out of the house! You might discover nifty coffee spots, like Lorca, Espresso NEAT or Caffeine.

Don’t try to “juggle-date” several women at once. Just. Don’t.

Do savor the finer restaurants of Fairfield County—like Westport’s The Whelk—when dating.

Don’t give up: If your dance card isn’t punched on Friday or Saturday nights, visit a gym, like Equinox, and work out. Self-improvement is NEVER overrated!

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