The Best First Date Questions to Ask

The Best First Date Questions to Ask

"What’s your sign?” didn't make the cut

By Brittany Hammonds | Last Updated: Jan 9 2023 | 7 min read

The best first dates are the ones where your drinks go undrank (undrunk?) because you’ve just been chatting (and flirting) for hours. On a good first date, time seems to flow faster than a keg at a college tailgate. So, what’s the key to great conversation on a first date? Great first date questions.

If you met online, you probably already know the answers to the old standbys. “What do you do?” and “Where are you from?” were right there in their profile.

At this point, you’re after deeper and more interesting connections. So, write these on your arm, type ’em in your phone, just do what you have to do to be the most interested (and therefore interesting!) first date she’s ever had.

Try these first date questions on your next night out:

“How has your day been?”

rita ora gif

What makes it a great first date question:

If you were to stop reading after this section I would be very sad, but also feel pretty great about leaving you with this one super-important question to kick-off any date.

Why is it so sneaky smart?

Because asking about a person’s day in a tone that feels familiar creates an unexpected intimacy.

It invites them to jump into a story about their boss, or a school project, or the call they just got off with their mom where they found out their beloved beagle Benny is being put down.

Okay, hopefully not that last one, but it invites the other person to hopscotch into something fun. Rather than starting with the banal, “Where did you grow up?” stuff.

Don’t get me wrong! That stuff is important! But it’s more fun coming out as part of a story, rather than the story itself.

We all keep a pocket full of “date banter” to pull from (and that’s to be expected), but it can also get in the way of – you know – actually communicating as simply as two friends would.

Why it’s revealing:

Starting with a question you’d pose to a pal can remove the filter we create in our subconscious (or very conscious) dating persona.

After this tone is set, you’ll be able to see what someone pays attention to during the day.

Do they only point out complaints? Do they relay their happiest moments? Sometimes keeping it simple can share the most.

“What’s your story?”

true story gif

What makes it a great first date question:

I love this question.

I root for it in the way we brag about our favorite athlete’s stats – springing at the chance to explain its greatness to anyone who’ll listen.

Why it’s revealing:

Specifically asking “What’s your story?” is an admittedly bold move.

It requires reading the conversation like you would an opposing team’s offense. And it encourages your date to tell you exactly why they’re interesting, almost like a challenge.

A challenge that’s especially exciting because it’ll give her the space to unabashedly share what makes her unique.

It’s the type of inquiry that puts the ball in the other person’s court – nay, it puts every piece of equipment in their possession because they can steer their answer in any way they choose, like detailing:

a general passion

favorite hobbies

past personal journey up until this point

physical journey that led them to X city, OR

how they describe their True Self (we’re getting deep here, y’all) to someone else

When this question was first posed to me, I was elated to have such an open-ended option. 

It pulls out a person’s priorities without coming off like you’re prying.

I’d dive into the intersection of where my passions meet my career, while someone else might describe their family or why they chose to move to the city they live in.

Discovering what question is important enough for someone to answer is enlightening in itself.

“What makes you roar with laughter?

martin laughter gif

What makes it a great first date question:

According to a series of experiments, sharing a laugh promotes social bonding on par with patting someone on the back or delousing (I mean, I’m all for light physical contact during a promising date, but I’m also hoping that contact doesn’t involve removing fleas from my date’s scalp).

And if you’ve ever been on the apps, you know that a “good sense of humor” is nearing the top of every potential mate’s list of Must Have’s.

But here’s the catch, what’s hilarious to you may not be tickle my funny bone, and vice versa.

If your favorite comedy is Tommy Boy while your date is more of a “chuckles at the cartoons in the New Yorker” kind of gal, your perspectives on other values may also differ on a larger scale.

Humor plays a leading role in how two people interact, so discovering each other’s temperaments now will be a shortcut to future laughs together.

Why it’s revealing:

You’ll be hard-pressed to find someone who abhors laughing (which is probably a good thing because that person would be the worst).

That being said, we can’t change what people find funny and if you’re like me, you’ll want to know as soon as possible if someone will laugh at your jokes.

“What’s your favorite part/memory of ____?”

schitt's creek marinating in memories

What makes it a great first date question:

While researching advice from the internet’s vast rolodex of dating experts, I quickly went from “This is an interesting question” to “Oh come on, a T.G.I. Friday’s-sized margarita couldn’t even help me find a natural way to say this” after realizing some questions are best left to learn overtime versus crammed into a span of two cocktails.

Sure, asking about someone’s favorite third grade teacher would provide insight into their favorite subject or mentor, but I’ve yet to engage in a first date conversation involving primary school recaps.

This is why I like to make a case for narrow – yet pertinent – questions that won’t sound like you’re ticking boxes on a “48 First Date Questions You Have to Ask” list.

For instance, if your date mentions an upcoming trip to their hometown you could ask, “What was your favorite part about growing up there?”

Or, if she credits an especially great professor with her decision to become a teacher, you could ask about her favorite lecture.

See what we did there?

Narrow questions that elicit deep answers without interrupting the flow of conversation.

Why it’s revealing:

A strictly defined set of first date questions may actually deter a great conversation (and remember the whole plan you made earlier to have a conversation at a set time?).

So, look for opportunities to get detailed information when it A) genuinely interests you and B) makes sense.



Here’s a list of bad first date questions to avoid at all costs:

  • “How much do you make?” I beg you. Please avoid finance discussions or attempt to pull out any form of documentation* to casually show off your income. *Yes, this is a real thing that happened. No, I’m still not sure how or why.
  • Anything that has a perceived right or wrong answer. If you determine compatibility based on her desire for three kids versus five or a preferred presidential candidate, you’re setting yourself up for first date disappointment.
  • “What do you think of me?” See above.
  • “Why are you single?” This question is rarely meant in an insulting way, but it can come off accusatory in a hurry. Furthermore, it will immediately beg the reply: “Why are YOU single, huh?”