33 Actually Good Questions to Ask on a First Date

My friend Liz Roche and I realized there was a problem — when we went on first dates, we had questions that we tended to ask, but we didn’t actually… like them. While things like number of siblings, living situation, and the infamous “cats or dogs?” are important to know about a future partner, they’re purely informational, and don’t tend to tell you a lot about the way someone’s brain works.

Thus, over several months, we gathered a list of questions that actually make for good conversation. A note: some of these are broad, and that’s intentional! Either you can clarify the question together (cute), or just interpret it how you want to, which in itself tells something about your personality. Wowie!

Without further ado, here they are:

When did you realize you were hot?

What reboot of a classic would you want creative control over?

If you could go back and choose a different college major, would you? (if they went to college)

What do you have that you prize, besides your laptop/phone?

What’s the most off-brand thing about you?

How have you personalized your bedroom?

Do you think your parents are in love? (if they’re together)

If you could see any performer, living or dead, live on a stage, who would you choose?

What pages do you have bookmarked on your computer?

If you had a series of genitalia pictures and a list of everyone you’ve ever seen naked, do you think you could match them up successfully?

What’s a song about wanting something that you feel is most in line with your own desires?

In what setting are you most relaxed?

If you had to pick a celebrity to hug you and tell you ”everything’s going to be ok,” who would be the most comforting to you?

What’s a piece of cultural ephemera you think about more than the average person?

What are three adjectives you’d use to describe yourself and one adjective that describes you the least?

What’s your favorite system of ordering the universe (religion, astrology, enneagram, etc), and what’s the most important thing it’s taught you about yourself?

What’s a specific skill that you’re better at than the average person?

If you could go back and change one thing about how you handled high school, what would it be?

What food or drink immediately conjures up your childhood?

Which reality competition show do you think you’d have the best chance of winning?

What celebrity do you feel like could be related to you?

What’s your favorite thing to do with your parent(s)?

What is something minor that someone said to you or about you, good or bad, that you think about a lot?

If you were a cartoon character who never changed clothing, what would your outfit be?

Do you make your bed?

What do you do when you find a bug in the house?

What combination of two fictional characters do you feel like describes you?

What would your middle school self be most surprised/pleased to find out about your current self?

Do you like your name?

Were/are you good about wearing your retainer?

What movie terrified you as a kid?

Are there any songs that transport you mentally somewhere when you hear them?

What’s the softest piece of clothing you own?

We hope you enjoyed this silly little listicle. If you ever use these questions on a date, please let us know how it went!