10 Conversation Starters for Even the Most Painful First Dates

You can only read the menu so many times before eventually deciding on the lasagna, lowering the wine list, and making grown-up conversation with your date.  For the nights when the witty dialogue you rehearsed in front of the mirror is failing you, pull out these go-to conversation starters to silence the metaphorical crickets. 

“Tell me about your family. Brothers? Sisters?”

Families are complicated. Everyone has a crazy uncle or a messy divorce or a long-lost twin that they’re not trying to bring up over appetizers. But they also have funny stories that you’ll relate to—who hasn’thad a weird family secret revealed at Thanksgiving after Grandma got a little too tipsy. By asking about his family without prying or probing, you can learn a lot about your date.  And maybe even his equally handsome long-lost twin!

“So are you a movie person or a TV person?”

Warning: Do not ask this question if your taste in either movies or TV shows is incredibly lame. (“Oh you like The Godfather? I’m a huge fan of Stomp The Yard…”) But, if you watch a show you’re not embarrassed to admit you enjoy—generally speaking this excludes all Bravo, TLC, and Oxygen programming—ask away.  And don’t let him get away with worshipping Weeds when everyone knows Breaking Bad is better.

“What’s the best trip you’ve ever been on?”

You don’t need to have traveled the world to have interesting stories from amazing trips. Don’t hate on your date if he hasn’t been to Milan, but think twice if he can’t stop talking about a sleazy spring break booze cruise.  Maybe he went on an “epic” road trip with the boys, or a family-vacation-turned-awesome—it’ll get you talking!

“Have you ever been on a truly horrible date? I feel like they’re fake, right?! Like out of bad chick flicks.”

As long as his answer isn’t, “Well, I mean, this date is up there,” you’re good to go. Either he hasn’t been on any horrible dates (in which case he’ll admire your perceptive observation) or he has hilarious stories (in which case you can laugh at another girl’s misfortune… oh, relax, no one needs to name names).

“So how’d you pick this place [or activity]? Is there a story there?”

Even if the castle you’re touring isn’t his family’s summer property (it could happen!), chances are there’s a reason he brought you to that particular spot.  Whether there’s a great story behind the linguini with clams or it’s just his favorite restaurant, you’ll spark conversation. And finally find out why he insisted you order the linguini with clams.  


Rachel Peck is a senior at Barnard College, Class of 2012, where she is majoring in English and Theatre and minoring in Women's, Gender, and Sexuality Studies. Although she admits to actually enjoying high school in her hometown of Bexley, OH, her favorite thing to do is explore her new--slightly more exciting--home, New York City. When she isn't watching good (and bad...) TV, finding excuses to plan dinner with friends, window shopping, or napping, Rachel enjoys working for the Barnard admissions office, serving on her sorority's various boards, and writing for whoever will read it.  You can also follow her on Twitter (@peckrachel) if you're into that.

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