Flirty questions to ask a guy and make him take notice

You two have been texting for some time, and while the conversation is fine and active, you’re looking for a way to take it up a notch in the romance department – while still staying light and engaging.

Naturally, you start thinking up flirty questions to ask a guy. But you want to show him you’re interested – and maybe even put some new romantic ideas in his head – without coming on too strong or aggressive. Let’s look at how you can do that naturally and humorously, without overthinking it or saying the wrong thing.

Some general tips on how to ask flirty questions

Before you unleash your arsenal of flirtatious one-liners and smiley-faced devil emojis, let’s look at the right flirty questions to ask a guy, as well as the right time and way to ask them.

• Try to be authentic. While you are being a little sexier and more daring, your flirting should always sound like your natural voice and fit your personality.
• Use humor. Flirting can be a bit tense for both parties (in the best way, obviously) but you can diffuse some of that tension with humor when you flirt.
• Keep it on the right level. The right flirty questions to ask your crush are not the same as the ones you’d ask of a long-term partner.

You can see that the way you flirt is as important as what you say when flirting. If you’re wondering how to flirt more effectively, check out these examples of flirty questions to ask a guy for some fun ideas and inspiration.

Flirty icebreaker questions

Before you ask, you can and should be a little flirty in your opening message, particularly if you’re using an app and want to distinguish yourself a bit and make your interest known. Using flirty questions to ask a guy right out of the gate shows them you’re confident, fun and aren’t afraid to take the lead in situations.

1. What’s been the highlight of your day? Besides me texting you.
2. You have such a cute dog. He doesn’t mind strangers petting him right?
3. Do you know any funny pickup lines for cute girls? I could use some.
4. How does the rest of your month look? Any space for me in there?
5. So glad we matched. Something about your profile really got me curious.
6. You seemed like you’d know where to get the best pizza in this neighborhood. Am I right?
7. You have a really nice face. Does the rest of the personality match?
8. Any crazy/funny roommate stories?      
9. If I used my worst pickup line on you, would you still take me for coffee?
10. What’s your favorite part of town to get a drink on a night like this?  

Flirty questions to ask a guy to make him laugh

Research shows humor plays a profound role in attraction¹ so it only makes sense to include some levity and playfulness in your repertoire of flirty questions to ask a guy. As said, it can help ease the sexual tension while showing a different side of you, along with your romantic intent.

1. If you had to rename me using the title of a famous song, which one would it be?
2. What’s a guilty pleasure movie you’d be embarrassed to show me?
3. If you were ever caught in a zombie apocalypse, would there be room for me in your van?
4. Would you stand me up if I showed up to a date in sandals and socks? 
5. What’s the cringiest line you’ve ever used to ask someone out? I, uh, need it for something.
6. Would you be willing to date someone whose love language is sending Spongebob Squarepants memes?
7. What’s the dumbest shower thought you’ve had?
8. Can you promise that if we went on a date, you wouldn’t end up being 12 squirrels in a trench coat? I’ve been burned before.
9. If we shot a podcast together, what do you think it would be about?
10. What kind of cat do you think I’d be, warm and snuggly or a couch/curtain ripper?

Fun flirty questions to ask a guy

This is more for when you want your style flirting to be somewhat silly and humorous. We do this to avoid coming off too strong, or when we’re just a little too nervous to be overly direct.

1. Have you ever been skinny dipping in the winter?
2. What’s the weirdest excuse you’ve used to get out of a date?
3. I promise I won’t laugh but what’s your most embarrassing sex story?
4. Who was your first-ever celebrity crush?
5. If we were in your car right now and just drove and took a holiday where we ran out of gas, where would you you want us to end up?
6. How many taco trucks do you think we could marathon in a day before we passed out?
7. What’s the craziest thing you’ve ever done/would do for a girl?
8. What date idea gives you the ick? For me, it’s going to play mini-golf.
9. What’s the most embarrassing thing you’ve ever ended up doing on a date?
10. What’s your best dad joke? 

Deep flirty questions to ask a guy

Conversely, being flirty and profound can also pair beautifully, particularly if you’re trying to reveal a more three-dimensional aspect of yourself. Using these flirty questions to ask a guy in the right way can also reveal deeper aspects of yourself to them, while showcasing how well you’ve come to know them.  

1. Tell me something you’ve always wanted to do but haven’t gotten the chance to.
2. What’s one thing an ex has done to you that you could never forgive?
3. What’s your attitude toward monogamy in a romantic relationship?
4. If you could share one moment in your life with me. Have me there. Which would it be?
5. What’s the first thing you noticed about me when you saw me?
6. Why do you think your last relationship ended?
7. What’s the worst thing I could ever do to disappoint you?
8. If we could escape together to any fictional place in the universe, where would we go?
9. Do you think you could ever believe in love at sight?
10. If I told you I couldn’t lie for the next 10 minutes, what questions would you ask me?

Flirty truth questions to ask a guy

While these may not be the right flirty questions to ask your partner or long-term boyfriend, they can help improve your intimacy, trust, and closeness in a new budding relationship by turning sharing into a flirty game of truth or dare.

1. What did you think about me when you first met me?
2. What’s something small you’ve always hidden from me?
3. What color underwear do you have on right now?
4. Have you ever thought there was something more to our relationship?
5. Have you ever gone on a second date after the first was a disaster?
6. Who was your first kiss with?
7. What’s a fantasy you’ve never shared with anyone?
8. What is something that’s perfectly mundane that you find weirdly sexy?
9. What do you tell your friends about us?
10. What’s the one thing that always makes you feel pretty? 

Low key flirty questions to ask a guy

Sometimes you want to play it cool while still send him something flirty; or you might just want to test the waters with some light flirting to see if he’s into it too. Here are some more subtle flirty questions to ask a guy.

1. Do you like horror? I really like horror movies but I need someone to watch them with or I get too freaked out. 
2. What are your plans looking like this weekend?
3. Are you going to the event next weekend too? I might see you there.
4. If you liked someone, how do you think you’d let them know?
5. What’s your favorite band? I think they’re coming to town soon.
6. What’s the most special thing someone can do for you?
7. There’s a new bar that just opened downtown. I really want to go check it out.
8. What are those tiny little things about someone that makes you fall for them hard?
9. Do you ever feel nervous around me? I feel that way around you sometimes.
10. What’s one movie or song you always share with people closest to you?

Flirty questions to ask a guy over text

Flirting over text can always be a bit nerve-wracking because you can’t immediately gauge their reaction, or read aspects of their body language to see if they reciprocate your flirty instincts. Waiting for a response can also feel like an eternity. But there are some effective flirty questions to ask a guy that capitalize on the text-and-picture format.

1. What attracts you to another person?
2. Guess what emoji I put next to your name in my address book?
3. What do you wear to bed at night?
4. What was the first thing you thought of me when we first met?
5. When you cuddle do you prefer to be the big or little spoon?
6. What’s your ideal kind of date?
7. Do you want to play a game? If I win, you take me out. If you win, I take you out.
8. What do you think makes two people compatible?
9. Why did you pick my profile out of everyone else’s? How did I catch your eye?
10. I’m desperate to try this new Korean barbecue place downtown. Want to go on a tiny adventure with me?

The right flirty questions to ask a guy should be sexy and fun for both of you

Being flirtatious early on, and down the line with your partner – as a way to keep the romantic spark alive – is probably the best way to keep conversations fun, light and engaging for both of you while still subtly (or perhaps sometimes not so subtly) showing interest, and that they hold a special place in your thoughts.

So try to use some of these flirty questions to ask a guy the next time you’re interested in one. But always remember that confidence, sexiness and good timing are just as important in making sure they all land the right way.