You know what’s awkward? First dates. Particularly of the blind variety (kudos to Hellen Keller for that). You met this great, really cute girl, hit it off, got her number, etc, etc, and you want to hang out with her again. But now what?

Do you go out to a nice restaurant for dinner? What if you have nothing to talk about? What if the food is bad? What if you have NOTHING to TALK about?!

Okay, how about a movie then? But what if she thinks that means you don’t want to talk to her? What do you even talk about after the movie? Do you put your arm around her?


Undoubtedly, an awkward first date can kill the chance of ever getting a second one, despite any chemistry that may or may not be present. So why gamble with something as intimate as a candle lit dinner or something as antisocial as a movie? What if instead, you and that special stranger did something that would be enjoyable even if you we’re doing it by yourself?

Without further ado, here are ten fun first date ideas that can almost guarantee you a second one:

1. Brick Oven Pizza Making

Riddle me this: What does every person in the world love? Before you go all stage-5-clinger status and get her a puppy, let me clarify that I’m talking about pizza. Swing through this west village spot to learn all the basics of crafting the food of the gods. At least now, when you two sit down for that awkward dinner, you’ll have a brand new shared set of skills to talk about…and pizza.


2. A Stand-Up Comedy Show

It’s like the movie’s more social (slightly drunker) older cousin. And unlike your typical AMC Lowes or Metroplex, its actually encouraged to be rowdy and loud at most comedy clubs. Laughter creates endorphins, which makes people feel bonded together, so it’s like you’re paying someone else to make your date fall in love with you! Kick back with your love interest and a few brews, and let the comedians do all the work. ProTip: extra useful for people who aren’t particularly funny or charming (we know you’ll win ’em later with your heart of gold, kid.)

3. Tango For Two

You got them moves like Jagger? Why not show ’em off with a fun tango class for you and what’s-her-name! Glide across the dance floor and shake those hips to whichever you prefer; the rhythm of the music or the beat of each other’s hearts *GAG*. Got two left feet and a good sense of humor? Have a wonderful night full of dancing AND laughter from self-deprecating jokes, a two-for-one deal.


4. Central Park Bike Tour

Ah, Central Park, Manhattan’s personal little snow globe, a pristine patch of nature surrounded by smog and skyscrapers. Take full advantage of the romance that is Central Park in the spring with a bike tour, cruising around Strawberry Fields and The Great Lawn on tandem or single bikes (tandem only if you really think it’s really gonna work out). If it’s a bust, at least you’ll get in a nice workout.

5. Beer Crawl Around Brooklyn

You know what’s easier than making small talk with a girl you barely know? Making small talk with a girl you barely know while drunk! Sample some of Brooklyn’s finest brews, all while getting to know your date in a comfortable (re: drunk) group setting. It’s also almost casual enough to play it off as a ‘just friends’ kind of date if things go flat (<–beer pun)

6. Chocolate Walking Tour

There is nothing more love-inducing than sweet, wonderful, dreamy, chocolate. Have fun sharing some indulgent treats, ranging from truffles to cake to hot chocolate, perhaps sharing with two straws… or hogging it with one. We won’t tell anybody.

….jk, get your own.

7. BYOB Painting Party

Even if you’re not a Picasso, or even a Pollock, for one night you can make any lady’s fantasy a reality when you paint her like one of your French girls at this booze-encouraging art studio. Don’t be afraid to get creative, but stay away from abstract art when capturing your date’s likeness — ovals and circles don’t exactly make for the most flattering portraits.

8. Archery Lessons

Head on down to Queens to learn the basics of this arrow shooting sport, a guaranteed favorite for any Hunger Games fans (i.e. everyone). Don’t be afraid to embrace your inner “District 1” competitive spirit, but please, for the love of the Director, only shoot at the targets (it’s not THAT kind of competition, everyone is allowed to make it out alive). May the date be ever in your favor.


9. Manhattan Night Tour

Is your gal a Manhattan n00b? What better way to get her acquainted with the best city in the world than with an after hours walking tour, where you’ll visit iconic sights like Times Square, Bryant Park, the New York Public Library, and 30 Rock. The best part is, if it doesn’t work out, you don’t have to sweat it cause IT’S FO’ FREE.

10. Trampoline Class

Remember how your parents never let you get a trampoline because they’re “too dangerous” or “too much of a liability?” Well, now’s your chance to throw caution to the wind and reclaim your youth. In fact, if everything goes well, perhaps your inner child won’t be the only thing you’re embracing that day *wink wink*.

None of these date ideas floating your boat? Play the Vimbly game to receive a personalized list of suggestions.

Happy dating!