Categories: Sex & Dating

20 Flirty Questions To Ask Your Crush

Now is a great time to learn more about those we hope to have a relationship with. If you’re a shy person and have a hard time talking to people, now is a fabulous time to attempt it through text or call. You don’t have to be in front of them, and if you’re texting, you can take your time answering them, so you don’t feel like you’ve been put on the spot.

Take the chance and send that first message. If you don’t know what to ask, that’s ok. I’ve scoured the web to find 20 of the flirtiest questions to ask your crush. 

These 20 flirty questions can help if you’re worried about sounding boring and uninteresting. They can also help you learn about them in a covert way!

If I could take you on a date anywhere in the world, where would you want to go?

Learn their dream destinations! This is actually one of my favorite questions to ask when I’m learning about someone new. They will often give you the reason why they want to go there as well. It can be a great way to learn a little about the things they want to do and some of their dreams!

What do you think is your best feature?

A great question to ask to learn what their favorite part of themselves is.

What do you think about before you fall asleep?

Learn about their last-minute thoughts! Do they stress about the things they didn’t get done that day? Or do they think about what needs to be done the next day? Or maybe…just maybe…they think about that special someone before they go to sleep!

What’s the Perfect Way to Ask Someone Out?

Learn what they might enjoy. This is a great way for you to find out how they would want to be asked out. If they would prefer to be asked in a sweet, romantic subtle way, or if they can handle a straight to the point “would you like to go out” kind of approach.

What is your wildest sexual secret that you want to indulge in at least once in your lifetime?

Get a little racy and learn about their deepest sexual desires!

What Are Your Top 3 Things to Do on the Weekend?

Maybe get some ideas for a date! This can lead you to what they like to do in their time off. In their free time. This can give you several different ideas for things to do when you do finally ask them for that date. It gives you three different options.

If You Had All the Time and Money in the World, What Are 3 Things You Want to Do?

Learn about their dreams! Learn about the things that they want most in life!

What Are You Most Scared to Do?

Learn about their fears! This one can help you figure out their vulnerabilities. But, for the love of God, please don’t do it so that you have something to use against them. Learn about what they fear so that you can help them conquer it if they want, or to help them avoid it if that’s what they want.

What Is the Nicest Thing Someone Could Do for You?

Learn about who they are! A great way to see what they feel are kind acts.

What’s your idea of the perfect date?

A great way to find out what they’d want to do on a date if they got to plan every aspect of it.

What is your biggest turn on?

Learn about their deepest desires!

Do you like when the girl makes the first move or would you rather be in control?

I like this question because it allows you to learn about how they feel about women who make the first move. Do they find it intimidating, or do they find it sexy?

What do you wear to bed- if anything?

Learn something a little more on the sexy side.

See Also

Would you prefer to make out or cuddle? Or make out, then cuddle?

Learn which one they prefer, so you know which move to make first when you finally get that first date…or the thirtieth one when you’ve gotten to the point of sitting in and cuddling! Another one of the most flirty questions.

What is the most embarrassing moment you’ve experienced in your lifetime?

Learn something about what made them who they are today. Another one of my favorite flirty questions. It may not seem all that flirty, but it’s a great way to hear a story about what truly made someone. How they learned an embarrassing lesson or something embarrassing that happened to them.

Can you tell me your funniest childhood memory that you can remember?

Learn about their childhood and the things that made them laugh. Learn about how they grew up with this flirty question.

While having sex, would you prefer getting on top or staying down in bed?

Learn about their moves and the way they enjoy sex! Definitely one of the more dirty flirty questions!

Are you seeing someone now?

Learn if the person you’re crushing on is seeing anyone at this time. A precursor to the next question if they’re not currently seeing anyone!

Are you looking to get a boyfriend/girlfriend anytime soon?

This one will help you learn if your crush is ready to date at the moment. Depending on what’s going on in their life, they may not be ready, but this will help you determine whether you should make that move and ask them out!

Wanna go out tonight?

Creme de la creme of flirty questions. Straight forward and gets to the point. Find out if they’d like to actually go out tonight. If tonight doesn’t work, perhaps you can work out another night that might work for the two of you to go on a real date!

Are there any flirty questions you asked your crush when you first started talking that worked like a charm? What was it? For those who are just starting, will you be trying any of these questions? Let us know in the comments!

Featured Image Credit:
Tricia Appelgren

Lucky mom of three beautiful children ages 9, 11 & 12. I graduated with a double bachelor's degree in 2015 from Ashford University. One in Journalism and Mass Communications and the second in Public Relations and Marketing.

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