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First date ideas: Pick the best spot for your personality

Never have first-date jitters again at these five potential locations for your first date. Find out which one’s best for you, and where to go.

By Drew Toal |
 (Photograph: Lizz Kuehl)
Photograph: Lizz KuehlRosemary’s Greenpoint Tavern
Brooklyn Bowl
 (Photograph: Samantha Miller)
Photograph: Samantha MillerStumptown Coffee Roasters
 (Photograph: Daniel Krieger)
Photograph: Daniel KriegerThe Dead Rabbit

As if planning a first date wasn't nerve-racking enough, you have to deal with the fact your choice in an initial meeting place implies something about your personality. Pick a snooty wine bar and your date might consider you pretentious; suggest a walk in the park and your mate might think you cheap. Take the guesswork out of picking a first-date spot with this guide; we've considered the pros and cons of five types of venues, and even gauged your chances for a second date.

RECOMMENDED: See the best date ideas in New York City

Photograph: Lizz Kuehl
Bars, Sports Bars

Dive bar

icon-location-pin Williamsburg

The vibe: Weird art hangs behind the bar, one needs a urinal Rosetta stone to decipher the bathroom graffiti, and the bartender will get your date another $3 happy-hour PBR when he’s damn well ready.
What that means for you: Dive-bar enthusiasm may not scream high-class marriage material, but a hole-in-the-wall should provide plenty of opportunities to get to know your date’s personality (and possibly see how handy they are in a bar fight).
Don’t do this: Use the relatively cheap drinks as an excuse to get hammered and play Bryan Adams anthems on the jukebox. That’s not as ironclad a method to get lucky as it might seem when you’re drunk.
Chances for a second date: The scuzzy dive is a good litmus test for people who want to date people who like scuzzy dives. You’ll know early on whether or not it’s going to work.
Where to go: Rosemary’s Greenpoint Tavern

Things to do, Concerts

Bowling alley

icon-location-pin Williamsburg

The vibe: Fun and lively, hitting the lanes is a nice option if you’re worried about having to maintain conversation over the course of an evening.
What that means for you:
Bowling can be a goofy, low-pressure dating activity. On the other hand, things could go south quickly if your date’s hand gets stuck in the ball return. 
Don’t do this:
Be super competitive. Keep things loose; the last thing anyone needs is to get a pitcher of Bud Light dumped on their head for doing the dirty bird after rolling a turkey.
Chances for a second date:
Better than your chances of picking up that seven-ten split.
Where to go:
Brooklyn Bowl,

Stumptown Coffee Roasters
Photograph: Samantha Miller
Restaurants, Coffee shops


icon-location-pin Greenwich Village

The vibe: Coffee may be code, in some circles, for sex, but meeting at a hip joe joint is bold (and not just in terms of the rich, flavorful beans). Without the aid of alcohol to smooth away jitters, it’s up to you to supply the entertainment.
What that means for you:
Going for coffee severely reduces the chances of a drunken hookup, but it’s a solid bet if you’re looking for more than a slobbery one-night stand.
Don’t do this:
Go to Starbucks. And while you might enjoy a half-caf, no-foam, extra-vanilla-soy-whatever on your own time, keep things simple; you don’t want to seem fussy from the get-go. (Your barista will thank you, too.) 
Chances for a second date:
Pretty high, unless you’re simply not simpatico. Casual, nonsloshed conversation allows you to feel one another out (figuratively) and get a sense of whether or not there’s a connection.
Where to go:
Stumptown Coffee Roasters,

Dead Rabbit
Photograph: Daniel Krieger
Bars, Cocktail bars

Cocktail bar

icon-location-pin Financial District

The vibe: Dark, dim and slightly intimidating, this place likely has “mixologists” rather than bartenders, and most of the drinks on the menu are served in a martini glass. What that means for you: Bringing someone to a swanky spot on the first date is a baller move. It means you’re taking the outing seriously, and as such, you should be taken seriously. It also means an empty wallet at the end of the night.
Don’t do this:
Act snooty just because your drink is a perfectly chilled mix of freshly squeezed juices, handcrafted bitters and top-shelf liquor. No one likes a hoity-toity jerk. (Also: If you’re going to pretend to be a big shot, don’t forget to tip like one.)
Chances for a second date:
Good, although setting a high standard early in the relationship might be laying the groundwork for a qualitative letdown later.
Where to go:
The Dead Rabbit,

Photograph: iStockphoto

Your couch

The vibe: Comfortable, familiar, smells slightly gamy. Sometimes the best first date is getting stoned and watching cartoons while sharing your extravagantly uncomfortable Ikea cushions.
What that means for you:
This is without question the most risky destination to suggest, but also the one with the biggest potential payoff. The question “Your place or mine?” is already settled.
Don’t do this:
Assume that everyone likes to pick Doritos out of the couch and use takeout napkins for toilet paper as much as you do. Spend a couple hours straightening up the place. Just because you’re not going out for a fancy dinner doesn’t mean your potential sweetie wants to smell three-week-old leftovers.
Chances for a second date:
This one is more about you than the venue, so bring your A-game. If you do land a callback, though, consider going someplace outside a five-foot radius of your TV.