Brittany Allen
July 30, 2014 11:38 am

First dates are the most stressful interviews of them all. It doesn’t matter whether you’re braving a Tinder date, a set-up or the first dinner date with a friend-with-benefits, the whole small talk thing can be really anxiety-provoking. You’re in the hot-seat and it’s go-time. So what do you do? Ask someone about their siblings? Banter about the weather, what school they went to and all that boring jazz?

There must be a more efficient way to suss out stranger-stranger compatibility. Of course there is. In the spirit of creativity, we came up with some alternative questions to ask on a first date. Hopefully, these slightly unexpected queries will kick off lots of good conversation, or at least keep things interesting for the duration of a drink.

1. So would you rather have a magnetic head, or skin made of porcelain? 

This is a goofy intro, for fans of ‘would-you-rather.’ But here’s what this hypothetical could reveal about a prospective partner: people who answer ‘magnetic head’ probably have an innate sense of curiosity. They’d like to be drawn into the world, despite potentially massive inconvenience. On the flip side, porcelain skin-types prefer to play it safe. They’d rather be fragile, and guarded. Perhaps their hearts follow suit?

2. If you had to be trapped in a laugh-track based American sitcom for the REST OF YOUR NATURAL BORN LIFE, which one would you choose? 

This one’s a cheeky way to figure out your date’s sense of humor. Not all sitcoms are created equal. If he or she is a Cheers fan, they probably care about community, and maybe possibly have a running tab at a neighborhood bar. A Cosby lover probably cares about family, first and foremost. That 70s Show-types enjoy hanging out in basements. These are just ballpark guesses, but you get the idea.

3. Do you think you’re doing “life” right?

Here’s an oblique, philosophical question, not for the faint of heart. It’s the kind of question that opens up a lot of conversation, without falling into the “what do you do for work?” trap. This one could also lead to a fun conversation about what success means for each of you, regardless of your fields. In any case, consider saving these big guns for dessert.

4. What’s the last book you loved? 

Pointed? Sure. Judgmental? Maybe. But perhaps John Waters put this best: “If you go home with somebody and they don’t have books, don’t have an adult sleepover with them!” Amen.

5. If you had a time machine, where would you take it? 

Here’s one way to learn about your date’s sense of curiosity (and historical knowledge). Is your person a rock-star on the inside, destined for Laurel Canyon in the 1970s? Would they prefer to be a conquistador, a pilgrim, a member of the Shogunate? Keep the constricting social mores in mind, and your sense of adventure UNBOUND.

6. What is a waste of your time, and what isn’t?

This is a fun way to rephrase the more-boring queries like, “what do you like to do in your free time?” By figuring out what your date finds worthwhile, you can learn about their entire value system. Do they consider waiting ‘a waste of time?’ Do they consider pleasure anecdotal to their mission in life? Useful things to know. . .

7. On a related note, what are your guilty pleasures?

You can learn a lot about what people are willing to admit being guilty of. Is it midnight bingeing? Workacholic-ing? Netflix? This is a nice way to break the ice, and lead a superficial conversation into the deep end.

8. What advice would you like to give your high-school self? 

And cue the trip down Memory Lane. It’s always fun to figure out who your prospective-date used to be, and how exactly they think they’ve changed.

9. You have 24 hours to steal a superhero’s power, costume, and secret identity. Whose would you snag? 

Spider-Man? Superman? Someone more obscure? This Q provides a learning opportunity for those outside the DC/Dark Horse/Marvel universe, and it’s also a neat way to see which “great responsibilities” your date would accept. Saving Gotham? Dominating the ocean, or the sky? Are they a sidekick, or a star? An outsider, a la the X-Men? And the conversation ball rolls down the hill. . .

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