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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?”

traveling road trip

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.  

“I fully acknowledge that this is a nerdy question, but do you have any good book recommendations? I actually need something new to read.”

Not every guy is a reader, so this question is not meant to be a test whereby you judge his intellectualism and self-worth.  If he’s never read Dostoevsky or Faulkner, that’s OK.  But maybe you’ve both read something recently that you can chat about or recommend.  Don’t turn the date into a book club—at least not without inviting me!—but literature and romance have been known to produce one another.  And it gives you something to talk about.

puppy adorable golden lab

“Are you an animal person? I feel like the world can be separated into animal lovers versus non self-identifying animal lovers.”

Follow-up questions include (but are not limited to): Cats or Dogs? Kittens or Puppies? Best YouTube animal video? Did you have an animal growing up? Oh, you’re allergic to animals and this was a weird thing to ask? Oh, I just came across as a crazy cat lady? Let’s move on…

“OK this is the deal breaker: what was the first CD you bought? No judgment.”

A nice point of entry into the “let’s talk about music and find out we both love the Beatles and then make out” conversation, without being so upfront.  No shame in admitting you saved up three weeks worth of allowance for a Spice Girls CD, because chances are at one point he knew every word to every Blink 182 single. 

“What’d you do last summer?”

i know what you did last summer movie

Asking what someone studies is boring. Asking what someone wants to “be when they grow up” puts the person on the spot.  Asking your date what he did last summer (besides being vaguely evocative of the 1997 horror movie) let’s him talk about his life in a concrete, interesting way.  Whether it’s humbly sharing top-secret information from a trendy internship or making you laugh with stories from a dead-end job, this question sets your date up for success. 

“Were you a Disney Channel Original Movie guy? One Saturday Morning? No? Just me? You didn’t grow up on Hey Arnold and Are You Afraid of the Dark?”

Nothing bonds two strangers like nostalgic reminiscence. And this is a discerning question to ask because, if he grew up in the United States between the years 1990 and 2000 and doesn’thave fond memories of Boy Meets World, you probably want to end things now.


If you can talk to your grandparent’s friends, you can talk to anyone.  Ask questions, resort to fallback topics, share stories from your own life, and remember that you’re on a date and not a job interview.  So show some cleavage.  Just kidding… kind of. Have fun.

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