The best (and worst) questions to ask on a first date

A few years ago, I was on a first date with a guy I’ll call Alexander. Finding a time to meet up was proving to be nearly impossible, so we settled on brunch at a hipster place in town.

Over pancakes and hot teas, we settled into a very pedestrian, first date line of questioning: where are you from? How long have you lived in Atlanta? What neighborhood do you live in? Do you have siblings? Oh, really? Where do they live?

Ugh, I’m falling asleep just thinking about it! I have been on so many first dates and answered these questions so many times that I can rattle off my answers while maintaining an entirely separate train of thought. I will truly make a mental to-do list while talking about how I grew to love Atlanta. If the date is really that boring, you probably won’t notice anyway.

And then Alexander threw me a curveball: what were you like in high school?

I hit pause on how many loads of laundry I needed to do when I got home. I thought long and hard. And I struggled. Look, in high school, I was really into matching my tube socks to my Goodwill t-shirts. I was in the marching band. I ate pastries for lunch. I was in the speech and drama club. I had some health issues. I never snuck out of the house. I had an early curfew and I lived in a sheltered world. I wouldn’t trade my high school experience for anything, because it was uniquely mine and it makes me me. But it’s not terribly interesting and I’m definitely not going to seem charming or impressive telling a stranger about it.

I get what Alexander was going for. I do! Fun, off-the-wall question to shake up the conversation. But it wasn’t the best question. What is?

Folks, it’s time to spice up your first date conversations. I’m here to help.

Before I dive in, here is a picture of my dog! Isn’t he cute? I’m quite certain he’d be in your dating profile photos if you owned him. Hold on, I have to tell you about the cute thing he did yester——

STOP. It’s a trap. Stop talking about your pets on first dates. Nobody wants to hear about your dog’s gas or see a video of him being a maniac after a bath. If I don’t have a pet, too, how am I going to keep that conversation going? It’s a rip tide and WE WILL NEVER ESCAPE OUR DESTINY OF BOREDOM.

Let’s start with the negative. Skip these questions. SKIP THEM.

1.) What do you like to do for fun?

Guys, you know what I like doing for fun? Sleeping. Tackling my Netflix queue. I like hanging out in my sweats with my friends drinking beers. None of those things are flattering and making me name my hobbies on the spot just makes me feel super lame. It is impossible to give an impressive answer to this question, unless you are impressed with how many episodes of Crazy Ex-Girlfriend I can watch in one sitting.

A humble suggestion for an alternative: what makes you laugh so hard you can’t breathe?

2.) What do you do/where do you work?

I’ll be frank: you probably covered this territory already on the dating app. Asking again might feel like you’re sizing your date up in a superficial way. I have a friend who hates this question so much that she started telling dates she’s a spy. At least she could tell if her dates are listening or not.

Maybe your date is between jobs. Maybe she’s going back to grad school. Maybe he really hates his job or his boss and talking about it seems torturous.

So, if you must go there, how about switching it up and asking, how would a 5-year-old describe what you do? In a city like Atlanta, rife with engineers, this might actually be useful if you’re trying to understand what on earth this person actually does for a living.

You could also try out: what do you love most about what you do? Most of us have something that gets us through long work days. Focus on that good.

3.) Let’s figure out who we know in common!

Ugh, SNOOZE. I don’t really care if you went to college a full 10 years ago with someone I barely know. Oh, you have a funny story about them? None of this is helping us get to know each other! Friend-in-common apps have made this a routine question, but honestly? Playing the “name game” of all your mutual friends is frankly dull, and doesn’t generate good conversation.

4.) Why is a girl like you still single?

This is NOT A COMPLIMENT. Yes, I AM YELLING. If I had the answer to this tiresome question, I would have given it to my grandmother a long time ago.

And if you ask me why I’m not married yet, I will probably light my hair on fire.

5.) How’d you get that scar on your arm?

Hoooooo, boy. Are you sure you want to know? Because it’s embarrassing and not in a cute, giggly way. SKIP.

Dishonorable mentions: Tell me about yourself (I won’t be able to remember a damn thing, and this is a lazy, unthoughtful question.). What’d you do last weekend? (You’re going to know I’m lying, because I was actually at home on the couch.)

And now, to the good stuff! This is my super-secret list of surefire ways to spark a fun moment on a date. Pull one out of your back pocket the next time you reach a lull in conversation:

1.) Where’s the most overrated — and underrated — place you’ve traveled?

This is a great alternative to asking for a list of every place someone has traveled and their favorite on the list. It’s hard to answer that question without feeling braggy.

Asking instead for their thoughtful perceptions of places is a great way to gauge how they see the world (literally). My most overrated? Charleston. Most underrated? Krakow, Poland. You’ll probably ask why. I’d love to tell you the reasons. I’ll have thoughtful answers.

Another great travel-related question: what’s the last adventure you went on, and what kind of adventure are you planning next?

2.) What’s the most classically MOM thing your mother does? What’s the most UGH, DAD! thing your dad does?

This is a great next-level question about family. And again, it provokes a thoughtful response. Maybe your dad wears earplugs during church worship music, like mine does. Maybe he loves his La-Z-Boy recliner so much that he’s worn a groove into the footstool with his feet.

Maybe your mom has an uncanny way of accidentally making sexual references all the time. Maybe you’ve realized over time that you feel scandalized when you see hickeys on teenagers’ necks, which is something your mom used to do. I have cried on a date from laughing so hard to the answers I got to this question.

3.) What’s your least favorite movie?

Tell me about the one movie you think is terrible that everyone else loved. Have you ever walked out of a movie? What movie did you think was so awful that you will actually defend its awfulness?

And fine, if you must know my favorite movie, ask me this: what movie will you watch over and over again, and without ever getting tired of it?

4.) Rank your top five favorite tacos in the city.

If you live in an amazing food town like Atlanta, you should absolutely talk about food. But please don’t ask me what my favorite food is. (Carbs.) This works great for any culinary genre that excites you: what are the five best burgers you’ve had in Atlanta? Top five favorite cocktails? Five best cups of coffee? Or my favorite: the five best doughnuts (there’s a correct answer!)

Bonus: if you and your date are both feeling the spark, you can use this to generate future date ideas!

5.) What celebrities did you have a crush on in middle school?

This question is purely silly. I had a huge crush on Jonathan Taylor Thomas, and the guy who discovered the Titanic at the bottom of the Atlantic Ocean.

Answering this question allows your date to be self-deprecating without embarrassing themselves, if they don’t want to.

Honorable mentions: How did you celebrate your 21st birthday? (This is usually a longer story.) What’s your go-to karaoke song?

Look, you don’t have to be an award-winning after-dinner speaker. But it’s not calculus, either: Try to set aside your mental to-do lists and listen to your date’s answers. Ask follow-up questions. Even if you aren’t feeling the person, or decide you aren’t attracted to them, this is a chance to get to know someone new, to engage in a conversation about something you won’t otherwise discuss. I have been out with all sorts of weirdos, and still found a subject we could both laugh about for a few minutes.

What can you learn? (Lots.) Can you share a laugh? (Yes.)

And don’t talk about your pets. Really.

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