50 flirty questions to ask your crush

Flirting with a crush can feel both exciting and terrifying. You don’t want to come on too strong, but you also don’t want to get stuck in boring small talk about the weather and work forever. That’s where the right questions come in.

Flirty questions are a subtle way to:

- Show interest without a huge, scary confession

- Create chemistry and inside jokes

- Find out if they might like you back

- Move things from “friendly chat” to “something more”

The key is to be playful, not pushy. A good flirty question doesn’t put your crush on the spot or make them uncomfortable; it opens a door for them to flirt back if they want to.

Below are 50 flirty questions you can use in person, over text, or on a call. They’re grouped into categories, and each one comes with a short explanation so you know when and how to use it.

Before we get to the list, a few quick ground rules.

Before You Start: A Few Flirty Ground Rules

1. Read their vibe.

If your crush is giving short answers, changing the subject, or seems uncomfortable, pull back. Flirting should feel fun for both of you.

2. Start light, then level up.

Begin with playful, low-intensity questions. If they respond well—joking, teasing, asking you things back—you can slowly move into more obviously romantic territory.

3. Make it a two-way street.

Don’t just fire off question after question. Share your own answers, stories, and reactions. Flirting is a conversation, not an interrogation.

4. Respect boundaries.

If they ignore or dodge a question, don’t push. Just switch to something lighter or more general.

5. Match the medium.

Some questions work better in person with tone and body language; others are perfect for text. If something might feel too intense face-to-face, it can sometimes feel softer over text.

6. Keep it fun, not explicit.

Flirty doesn’t have to mean graphic or overly sexual. Suggestive, sweet, and playful is usually more effective—and more comfortable—for most people.

7. Be genuinely curious.

The best flirty questions still come from real interest. If you actually care about their answer, it’ll show.

Light & Playful Icebreakers (1–10)

These are easy, low-pressure questions that add a flirty twist without going too deep too fast.

1. “What’s your idea of a perfect first date?”

This lets them show what they enjoy romantically without asking, “Do you want to go out with me?” right away. Pay attention to their answer—you can later suggest doing something similar “one day… together.”

2. “What did you first notice about me?”

A classic, gentle way to invite a compliment. If they mention your smile, eyes, or vibe, that’s a good sign they see you in a romantic light. You can always tease back with: “Wow, I’m flattered.”

3. “If we could sneak away from everything right now, where would you want us to go?”

This puts you and them in the same imaginary scenario, which is a subtle way of building a sense of “us.” It’s also a fun way to discover whether they’re more about beaches, cities, nature, or cozy cabins.

4. “Are you more into staying in with movies or going out and exploring?”

This is a casual question that can smoothly turn into planning a hangout. If they say staying in, you can say, “So you’re saying we’d be great at movie nights?” If they say going out, you can suggest a future adventure together.

5. “What’s the most random thing that instantly makes you smile?”

It’s playful but also a bit personal. Their answer might be cute animals, cheesy jokes, or a certain type of text. You get insight into how to make them happy—and you can later use it.

6. “Do you believe in love at first sight, or should I walk by again?”

This one is boldly flirty but wrapped in a joke. It works best if you already joke around a lot. If they laugh or flirt back, you’ve just raised the temperature in a fun way.

7. “What’s your favorite way to spend a lazy Sunday?”

This invites them to describe a cozy, intimate vibe. If their ideal Sunday sounds compatible with yours, you can say, “That sounds like my kind of Sunday… maybe we should try that one day.”

8. “What’s something small that instantly makes you think, ‘This person is attractive’?”

You’re giving them a chance to talk about what they’re drawn to, which can give you hints about how they might see you. If you match their description, you can jokingly say, “So basically… me?”

9. “Would you rather have a cute coffee date or a late-night walk under the stars?”

This frames romance as a fun choice. Whichever they pick, you have a built-in idea for a future date. And you can answer too, to see how aligned your tastes are.

10. “If you had to describe your ideal type in three words, what would they be?”

You get to see what they look for, and it’s easy to turn it flirty. If their three words match you even a little, tease: “Are you describing me right now, or…?”

Compliment-Based Flirty Questions (11–20)

These questions give them space to feel special while hinting at your interest.

11. “What’s a compliment you never get tired of hearing?”

This question is both sweet and practical. Once they answer, you know exactly what kind of genuine compliment will make them feel seen. You can even follow with, “Well, you definitely [insert their answer].”

12. “What do you think is your most attractive quality?”

People don’t often get to say what they like about themselves. It can lead to a deeper conversation about confidence and self-image—plus, you can respond with what you find most attractive about them.

13. “What’s something you wish more people noticed about you?”

This shows you care about more than surface-level stuff. Their answer might be about their personality, ambition, loyalty, or quirks. It can easily lead to you saying, “I noticed that about you actually.”

14. “What’s the nicest thing someone you liked has ever said about you?”

This ties romance and affirmation together. It encourages them to remember a time they felt desired, and you get to learn what kind of words touch them most.

15. “If I asked your friends why people have crushes on you, what would they say?”

Framed as a joking, third-person question, it lets them talk about their strengths in a fun way. If they’re shy, you can encourage them with, “Come on, don’t be modest…”

16. “Do you realize how [specific compliment] you are, or should I remind you more often?”

Make this specific—funny, thoughtful, stylish, charming, etc. It’s less a question than a flirty statement disguised as one, and it lets you give a direct compliment while staying playful.

17. “What’s your favorite compliment that I’ve ever given you?”

This only works if you’ve complimented them before. It shows that you remember your interactions and care how they landed. It also confirms that your words had an impact.

18. “If you could bottle up one thing about your personality and give it to someone, what would it be?”

Subtly flirty because you’re asking what makes them special, but in a thoughtful way. They’ll likely choose something they’re proud of, and you can say that’s one of the reasons you enjoy them.

19. “What do you think people notice first when they meet you?”

You can respond with what you first noticed. If it’s something flattering—like their laugh, eyes, or energy—that’s a soft, natural way to compliment them.

20. “Has anyone ever written you a love note or text that you still think about?”

Romantic without being explicit. It gets them talking about romance they’ve experienced (or wish they had), which helps you understand what feels meaningful to them.

Deeper Connection (But Still Flirty) Questions (21–30)

These help move you from surface-level banter to more emotional chemistry, while still keeping a romantic vibe.

21. “What makes you feel really cared for in a relationship?”

You’re basically asking about their emotional love language. Their answer is a roadmap for how to make them feel valued—attention, quality time, encouragement, small surprises, etc.

22. “What’s something you’ve always wanted to do with someone you really like?”

This encourages them to imagine doing that thing with you, even if they don’t say it out loud. It could be traveling, cooking together, taking a class, or just having long late-night talks.

23. “Do you remember the moment we stopped being ‘just acquaintances’ and actually got close?”

This invites them to reflect on your journey together. If they recall a specific memory, that’s a shared, meaningful moment you can build on.

24. “When do you feel most confident and attractive?”

This gives you insight into how they see themselves at their best. It also sets you up to say, “Honestly, I think you’re pretty attractive when you [insert something you’ve noticed].”

25. “What kind of chemistry do you think matters most with someone—emotional, mental, or physical?”

You’re asking about attraction in a thoughtful way. Their answer tells you what they prioritize and gives you a chance to share your own view of attraction and connection.

26. “What’s something small that instantly makes you feel close to someone?”

Maybe it’s deep talks, shared humor, supportive messages, or simple physical closeness like sitting shoulder to shoulder. Use their answer as a guide to how you can get closer naturally.

27. “Do you have a favorite ‘almost relationship’ story?”

This invites them to talk about times things nearly worked out. It can be funny, bittersweet, or revealing. It also quietly acknowledges that they’re someone others have liked—and that you do too.

28. “Do you think we’re similar or complete opposites?”

This plants the idea of “we” while letting them compare you. If they say similar, great—you can talk about shared traits. If they say opposites, you can tease, “You know what they say about opposites…”

29. “If we had met in high school/college, do you think we would have been friends… or crushing on each other?”

This lets them picture a different version of your lives where you might have liked each other earlier. It’s hypothetical enough to feel safe but still very flirty.

30. “What kind of moments make you think, ‘Wow, I really like this person’?”

You’re asking them to describe the feeling of falling for someone. As they talk, they may subconsciously compare those moments with things they experience with you.

Romantic Hypotheticals & Scenarios (31–40)

These lean more obviously romantic, but they stay fun and imaginative rather than intense or heavy.

31. “If we were in a romantic movie, what scene do you think we’d be in right now?”

Let them be as cheesy or realistic as they want. Their answer might be a meet-cute, slow-burn friends-to-lovers, or banter-filled scene. It directly frames you two as the main characters together.

32. “What song would you put on a playlist called ‘Crush Vibes’?”

Music is a safe way to talk about feelings. You can trade songs back and forth, and the playlist itself can become a low-key symbol of your connection.

33. “If you could slow dance with anyone right now, who would you pick?”

Bold, but still gentle. If you already have comfortable chemistry, it’s a clear invitation for them to either jokingly say “you,” or blush and dodge (which is still revealing).

34. “Would you rather have a surprise date planned for you, or plan the perfect date yourself?”

This reveals whether they like to feel cared for and surprised, or they enjoy being in control and thoughtful. Either way, you learn how they like romance to show up.

35. “If we got stuck together in an elevator for an hour, how do you think we’d pass the time?”

You’re placing yourselves in a slightly dramatic, intimate scenario. Their answer may include deep talks, games, or silly challenges—either way, it’s a “just us” fantasy.

36. “What’s your favorite ‘crush moment’ from a movie or show?”

This gets them to describe what kind of romantic build-up they find adorable or exciting. Those scenes often mirror what people want in real life, even if they don’t say so directly.

37. “If I told you I had a crush on you in the past, what would you say?”

This is a sneaky, semi-hypothetical way to test the waters. They might ask, “In the past?” which gives you an opening to clarify. Their reaction gives you a lot of information about how they feel.

38. “Would you rather stay up all night talking with someone or spend a whole day going on adventures together?”

Both options are romantic, so whichever they choose, they’re sharing the kind of connection they’d want—with you, potentially.

39. “Imagine we bump into each other in 5 years—what do you think our lives will look like?”

They might include you in their future, or just describe their individual goals. Either way, it gives you a glimpse of whether they can imagine you still being around.

40. “If someone asked me why you’re so easy to have a crush on, what should I tell them?”

This is a direct but playful way of saying, “You’re crush-worthy.” It’s almost a confession, but wrapped in a question that lets them respond however they’re comfortable.

Future & “Us”-Oriented Flirty Questions (41–50)

These are more forward, best used once you already have good rapport and some mutual flirting going on.

41. “What’s something you think we’d be really good at doing together?”

This can go in a silly direction (being chaotic in public) or genuine (traveling, cooking, working out). However they answer, you get them imagining shared activities—and therefore, more time with you.

42. “If we went on a date, what do you think would be the best part?”

You’re calling it a date out loud, which is more direct—but you’re still phrasing it hypothetically. Their answer might surprise you; often, people value the small moments, like talking or laughing together.

43. “Do you think we’d survive a weekend getaway together without getting sick of each other?”

This is both playful teasing and a “test run” of what they think about spending extended time with you. If they say yes, you can joke about destinations; if they tease you back, that’s chemistry.

44. “What’s something you’d want me to remember about you, even years from now?”

That’s a surprisingly intimate question. It says you expect to remember them for a long time, and it lets them choose what part of themselves they most want you to hold on to.

45. “If you could pick one moment we’ve had to replay whenever you’re in a bad mood, which would you choose?”

This forces them to pick a favorite memory with you—which is inherently affectionate. It also shows you which of your shared experiences meant the most.

46. “Do you ever wonder what people would think if they knew how much time we talk?”

This one assumes you already chat a lot. It acknowledges your closeness and lightly suggests that other people might see it as more than just friendship. It can lead to a “What are we?” conversation down the line.

47. “If someone asked me whether we’re just friends or something more, what would you want me to say?”

This is a brave, clear, but still open-ended question. It gives them the power to define things, or at least to hint at how they see you. Only ask this if you’re ready for an honest answer.

48. “What’s one thing you’re curious about when it comes to us?”

Emphasis on “us” subtly encourages them to think of you both as a unit. They might ask about your feelings, your intentions, or the future of your dynamic, which opens space for real conversations.

49. “Do you ever re-read our old messages?”

If they say yes, that’s a strong sign they care about your connection. If they dodge, you can tease them. Either way, you’re gently pointing out that your chats mean something.

50. “What’s the easiest way for someone to make you fall for them… asking for a friend?”

This is an unmistakably flirty question, but the “asking for a friend” line keeps it light. Their answer is almost a step-by-step guide to their heart—and they’ll probably suspect that “friend” is actually you.

How to Use These Questions Naturally

Having a list is helpful, but how you use these questions matters just as much as which ones you pick. A few practical tips:

1. Don’t rapid-fire them

Dropping question after question can feel overwhelming or scripted, especially if you’re clearly pulling from a list. Instead:

- Sprinkle one or two questions into a normal conversation.

- Let their answer breathe—ask follow-ups, tell a related story, or share your own answer.

- Treat each question as an opening, not a checklist item.

For example, if you ask, “What’s your idea of a perfect first date?”:

- Respond with your own ideal date.

- Playfully compare them: “Yours sounds way more romantic than mine; maybe we should combine them.”

2. Match your relationship stage

You don’t need to jump straight to “If we went on a date…” if you’ve only exchanged a few casual texts. A gradual build can look like:

- Start with light, fun questions (1–10).

- Move to more compliment-based and connection-focused questions (11–30) as you get comfortable.

- Save the future-and-us questions (41–50) for when it feels like there’s real mutual interest.

3. Use your own voice

You don’t have to copy these word-for-word. Adjust them to sound like you. For instance:

- Original: “If we went on a date, what do you think would be the best part?”

- Your version: “Real talk: if we ever went on a date, what part do you think would be the most fun?”

What matters is the intention behind the question, not perfect phrasing.

4. Handle awkward moments with grace

Sometimes they’ll:

- Give a short answer

- Change the subject

- Laugh nervously

If that happens, don’t panic or apologize too dramatically. Just:

- Smile (or send a lighthearted follow-up text)

- Shift to a safer topic

- Save deeper or bolder questions for later

You want them to associate flirting with you as easy and enjoyable, not heavy or pressured.

5. Be ready to share your own feelings

Some of these questions naturally lead to, “What about you?”

If you’re using them because you genuinely like your crush, be prepared to:

- Admit what you find attractive

- Say your favorite moment with them

- Hint (or state) that you do have a crush

Flirty questions are often the bridge between “I think I like you” and actually saying so.

Final Thoughts

Flirting isn’t about delivering perfect lines; it’s about creating a space where both of you feel excited, appreciated, and a little bit butterflies-nervous. These 50 flirty questions are tools, not scripts. Choose the ones that:

- Fit your personality

- Match your crush’s vibe

- Feel appropriate for where your connection is right now

Start light. Pay attention to their reactions. Let the conversation wander. And if you sense that your crush is flirting back, don’t be afraid to gradually be more direct.

If you’d like, tell me a bit about your situation—how well you know your crush, how you usually talk (text, in person, etc.)—and I can pick and customize the best 8–10 questions for you specifically.