21 Questions to Ask Your Crush: Fun & Flirty Conversation Starters

Co-authored by Mark Rosenfeld and Jessica Gibson

Last Updated: April 25, 2022

Trying to get to know your crush? Questions are a great way to direct the conversation or break the ice! You can also play games that are question-based like the popular 21 Questions. To help you get started, we've gathered 21 of the most fun, flirty, and thoughtful questions you can ask.

1

"What meme best represents your life?"

This is a silly question that can make your crush relax. It's such a disarming question that they can be as serious or lighthearted as they like when answering. Since meme humor is so all over the place, it's also a really good way to figure out if you two have a similar sense of humor.

2

"If you had to rename yourself, what name would you choose?"

Ask this question to get them talking about themselves. Give your crush a chance to explain the reason for the name they picked. They might say it's from a favorite book, it's the name of a loved one, or it's the name of one of their favorite places. Whatever they choose, you'll learn something about them.

3

"Who is your biggest celebrity crush?"

If your crush answers with a celebrity you like, you might have a lot in common. For instance, if you're crushing on a pop star, they might start talking about that artist's albums and what they liked about them.

4

"What's your favorite movie scene of all time?"

Their answer can tell you a lot about their personality. Plus, if you start going out, you'll probably be watching movies together, so it's a good idea to find out if you want them to pick the flick.

5

"Do you believe in astrology?"

Find out if your zodiac signs are compatible. If you check your horoscope every day, you're probably dying to know if your signs can hit it off. They might reply that they don't know their sign. If that's the case, you can just ask when their birthday is.

6

"What do you spend way too much money on?"

Your crush's spending habits give you insight into what they like. If they spend a lot of money on sneakers and you're a fashion junkie, you've just figured out a great way to connect. You two could enjoy a date night at the mall and you have a gift idea for the next birthday or holiday that rolls around.

7

"Who was your first crush?"

Ask this one to build rapport with your crush. After all, almost everyone has had a crush at some point! Open up and reveal yours, so they learn a little about you. Then, you two can laugh over your earliest crushes. Plus, if they're embarrassed about it, you can playfully tease them later.

8

"What's the wildest thing you've ever done to get someone's attention?"

This fun question helps you get an idea of what kind of person your crush is. If your crush answers with something pretty tame, you might get the impression that they're a reliable, stable person. On the other hand, they might surprise you!

9

"Do you find first dates fun or stressful?"

Your crush's answer will tell you what they like and dislike about dating. If they say they're stressed out by doing classic dates like dinner and a movie, you'll know to switch it up and try something casual. If they like first dates, pry a little bit to find out things they like to do.

10

"How many people have you ever kissed?"

Getting your crush to open up to you can make them feel more comfortable around you. Their answer can also paint a picture of their personality—they might be shy and hesitant to talk about other people they've kissed, or they may be talkative—it's a great segue to talking about past relationships.

11

"Who knows you best?"

Learn about the people closest to your crush, so you find out what they look for in a friend. Their answer might tell you if they're really close with their family or if their social circle comes first. It's just another way to gauge if you two have similar values. If family is super important to you too, you've got something in common.

12

"Would you rather people think you're funny, kind, or smart?"

Their answer helps you understand how your crush sees themselves. Specifically, you'll learn how they want others to view them. Maybe they were the class clown and they'll share funny stories. They might say they're kind if they empathize with others, or they may say they're smart if they appreciate logic. This question also opens the door for you to tell them what you enjoy about them.

13

"What's the last thing you think about as you fall asleep?"

Your crush can use this answer to flirt with you or share what's on their mind. They may admit that they think of you as they drift off! If they think about other things—like their worries or fears, it gives you two something to talk about.

14

"What's the weirdest thing you find attractive in a person?"

Your crush's response can reveal a different side of their personality. Usually, if they're into something weird, it's probably something they don't often mention. Being left-handed? Having freckles? Being awkward? You'll catch a glimpse of your crush's quirky nature with their response.^{[1]
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Research source}

15

"What's been your best day of the year so far?"

Questions like this are a good way to learn about what your crush likes. It also shows them that you're curious about them, and gives your crush a chance to describe a lot of things they like.^{[2]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach
Expert Interview. 11 June 2021.} Think of this question as homework for planning future dates.

16

"If you had unlimited money, what would you do with the rest of your life?"

Talking about their hopes gets you two talking about the future. Does your crush want to help out their family? Would they travel as much as possible? Maybe they want to learn a certain skill. Their answer will give you a glimpse of their hopes and dreams.^{[3]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach
Expert Interview. 11 June 2021.}

17

"Where do you want to be 5 years from now?"

Asking about their plans lets you know if you have similar goals. If you're hoping for a long-term relationship, it's important to figure out if your interests are aligned as a couple.^{[4]
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Expert Source

Courtney Quinlan
Matchmaker & Dating Coach
Expert Interview. 27 August 2021.} If they're hoping to score a job out-of-state and you're looking for something casual, you two might hit it off.

18

"What is one thing you can't live without?"

Ask this one to see if you have compatible values. If they answer with something that you can't stand, then maybe you two don't have similar interests. On the other hand, they may rattle off something that you also love.

19

"Is there anything you're wondering about me?"

Use this one to put your crush in charge of the conversation. They might ask you a really unique question that leads to an interesting conversation, or they may play it safe with a generic question. Either way, if they ask you a question, it gives you a chance to share about yourself.

20

"What was your first impression of me?^{[5]
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Research source}

This gives your crush a chance to flirt with you. It also gives you a great opportunity to take your relationship to the next level. Maybe you were at a party and they say they love your confidence and bubbly personality. Once they compliment you, ask them if they'd like to go out with the most confident person in the room.

21

"What's something you've never told anyone else?"

Give your crush the opportunity to share something personal. If they share a deep secret, they probably feel they can trust you—make a connection by sharing something really personal, too. If they share something silly, play along! Your crush will see that you're fun to be around.