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Delaney's Downloads: Crucial Questions To Ask On A First Date

Here are some Qs to bring you closer—or, if the person has some weirdo answers, weed ’em out quick:

1.“What’s the best vacation you ever took?”

Having different vacation styles isn’t a deal breaker, but if you love relaxing beach resorts while your date prefers having a stacked itinerary, you might want to know! Also, talking about your favorite travel memories (aka probs some of the best experiences of your life) is solidly fun, and who knows—maybe you both went to that incredible restaurant in Amsterdam.

2.“What’s your best friend like?”

Because friends tell you a LOT about a person and unfortch, you’re not likely to meet them on a first date, hearing about their bestie (or if they even have one) is the next best thing. If they gush about their BFF being a kind, loyal, hilarious person—great! If they barely have anything to say other than allude to being drinking buddies...hmm.

3.“Did you ever have a pet?”

You’ll learn a lot from:

–What kind of pet they had/have (a dog person is waaaaay diff than a snake one, just sayin’)

–How determined they were to get a childhood pet (even if it never happened, them making a powerpoint to try and score a cat is both adorable and tells you a lot!)

–Their saying “I don’t really care about animals” (Excuse me, what???)

4.“What’s the last show you binged?”

You won’t learn much from them also loving Game of Thrones, but knowing about a show they loved enough to forgo social plans for a few days is a diff story. At the very least, you might get some good Netflix recs.

5.“What’s your sign?”

Hey, astrological compatibility is a thing! But what’s even more important than knowing if they’re a Gemini or a Scorpio is if they’re the kind of annoying person who’ll judge you for reading your daily horoscope.

6.“What’s a food you hate irrationally?”

Normal answer: honeydew melon.

Run-for-the-hills answer: ALL vegetables or anything that isn’t plain pizza.

7.“Who’d you vote for?”


8.“Are you a morning or night person?”

Is the second date going to be at, like, 6:30 p.m. because they have to squeeze in a workout the next day, or can you chill and talk till 3 a.m. without fear you’re hindering sleep? It’s not the biggest hurdle to overcome, but it’s nice to get a sense of if your general lifestyles match up.

9.“What’s something you’re dying to try?”

With answers that could range from “a threesome” to “skydiving,” this low-pressure small-talk question can either give you common ground or make it all too clear it’s probably not meant to be.

10.“Do you like your job?”

This might seem basic, but the answer can reveal a lot about a person’s personality type. For instance, if they hate their job but are doing something to try and get a new one, that’s a good sign they aren’t going to be bitter and terrible and pessimistic. It also shows they have ambition, which, if that’s what you’re into, is great! Or maybe they don’t care much about their job at all, because work is something they just do to fund their personal life. In any case, you want to get a sense for how much work factors into a person’s life pretty early on.

11.“If you suddenly won $1 billion, what would you do?”

Look, whether or not that’ll actually ever happen, you can learn a lot about a person if they say “buy a castle on a secluded island and never work again” vs. “pay off student loans, buy my parents a new house, go to grad school for art, and donate to charity.”

12.“What’s the last good thing you read?”

You’ll find out (a) if they read at all, (b) if they explore beyond the canon of dead white guys, and (c) what to read next, if their tastes match yours.