Flirty Questions to Ask Your Crush While Texting: 115 Romantic Conversation Starters

Flirty Questions to Ask Your Crush While Texting: 115 Romantic Conversation Starters


Texting your crush can be exciting, but also nerve-wracking. You want to get to know them better and move things forward, but it’s hard to come up with flirty, intriguing questions.

Asking the right questions is key for sparking conversation with your crush. Flirty yet thoughtful questions can help you associate compatibility, gauge interest, and even start something romantic.

Flirty Questions to Ask Your Crush While Texting

This article provides 115 flirty questions to ask your crush over text. They range from sweet questions to break the ice, to deep questions that reveal more about their interests, values, and desires. Use them to get the conversation going, find things you have in common, and subtly hint you’re interested.

15 Flirty Questions to Ask Your Crush to Break the Ice

15 Flirty Questions to Ask Your Crush to Break the Ice

When texting your crush for the first time, you want to keep things light. Here are some flirty questions that can spark an engaging conversation:

  1. What’s your favorite emoji? This helps break the ice with some humor.
  2. Would you rather skydive or bungee jump? See if you’re both adventurous.
  3. What’s something you want to do this year that you’ve never done before? Get ideas for fun new dates.
  4. What’s your favorite drink from a coffee shop? Compare tastes and find future date spots.
  5. If you could have dinner with any celebrity, who would it be? This reveals their interests.
  6. What’s your favorite way to spend a day off? Look for common ground in hobbies and relaxation.
  7. If you could live anywhere in the world, where would it be? Find out their travel dreams.
  8. What’s your favorite season? See if you enjoy the same time of year.
  9. Would you rather be an amazing painter or brilliant inventor? Creative icebreaker.
  10. What TV series have you binge watched recently? Bond over shared shows.
  11. What’s your go-to order at a restaurant? Compare favorites.
  12. What would be your dream vacation? Romantic fantasies are a good sign.
  13. Do you have any pets? What are their names? Pet talk can lead to more intimate conversation.
  14. What emoji best represents your personality? Fun way to describe yourself.
  15. What are some small things that make your day better? Get a feel for what makes them happy.

25 Flirty “Would You Rather” Questions

25 Flirty “Would You Rather” Questions

“Would you rather” questions are a fun and flirty way to find out your crush’s preferences, values, and desires. They get some friendly debate going while revealing information about their personality. Here are 25 “would you rather” questions to ask your crush over text:

  1. Would you rather win the lottery or live twice as long? Gauge what motivates them.
  2. Would you rather always say everything on your mind or never speak again? Gets to honesty vs. sensitivity.
  3. Would you rather hike in a forest or lounge on a beach? Compares adventures vs. relaxing.
  4. Would you rather be able to fly or turn invisible? Imaginative and lighthearted.
  5. Would you rather have a lifetime supply of chocolate or cheese? Food and romance.
  6. Would you rather wear the same outfit every day or have to dress up for every occasion? Low-maintenance vs. high-fashion.
  7. Would you rather explore space or the ocean? Reveals their sense of wonder.
  8. Would you rather be the most popular or most intelligent person? Intriguing personality question.
  9. Would you rather only shop online or in stores? Compares preferences.
  10. Would you rather give up showers or give up coffee? Quirky and tells morning routines.
  11. Would you rather have unlimited international first-class tickets or never have to pay for food at restaurants? Compares wanderlust and foodie interests.
  12. Would you rather be able to teleport anywhere or be able to read minds? Imaginative scenarios show values.
  13. Would you rather have yourself always be photographed in the most flattering way possible or have an unlimited memory? Fun vanity vs. practicality.
  14. Would you rather be the funniest person you know or the most intelligent? Another good personality question.
  15. Would you rather travel 100 years into the future or the past? Compares interest in history vs. technology.
  16. Would you rather be able to control fire or water? Creative insights into their personality.
  17. Would you rather give up your smartphone or give up all sweets? Reveals everyday interests.
  18. Would you rather be able to fly or have super strength? Classic superhero debate.
  19. Would you rather have unlimited money to spend only on yourself or spend a limited budget but use it to help people in need? Says a lot about values.
  20. Would you rather be able to communicate with all animals or speak every language? Imaginative and compares interests.
  21. Would you rather live one life that lasts 1,000 years or 10 lives that each last 100 years? Philosophical look at mortality.
  22. Would you rather be the funniest or the wisest person in the room? Another way to get at humor vs. intelligence.
  23. Would you rather be able to go to any theme park in the world for free for a year or eat any food you want for free for a year? Compares playfulness and food interests.
  24. Would you rather be famous when you are alive and forgotten when you die or unknown when you are alive but famous after you die? Reveals thoughts on legacy vs. immediate gratification.
  25. Would you rather be stuck on a broken ski lift or in a broken elevator? Gets conversation flowing about fears.

20 Romantic Questions to Ask Your Crush

20 Romantic Questions to Ask Your Crush

Once you build rapport with flirty small talk, you can gradually ask more romantic questions to hint that you like them as more than a friend. Here are some sweet, thoughtful questions to ask your crush over text:

  1. Have you ever liked someone you didn’t think you should? See if you’re the “wrong” crush.
  2. What could someone do to win your heart? Flattering and gets insight.
  3. Where’s the most romantic place you’ve ever been? Ideal date planning info.
  4. How do you know when you have a crush on someone? They may drop hints about you!
  5. What’s your idea of the perfect date? Gives dating ideas and preferences.
  6. Do you believe in love at first sight, or should you get to know someone first? How to approach revealing your feelings.
  7. How do you subtly flirt with someone you like? See if you notice when they flirt.
  8. Do you think there’s one soulmate for everyone, or can you have chemistry with different people? Views on romantic possibilities.
  9. Have you ever written a love letter? Thoughtful gift idea if they enjoy them.
  10. What’s the most thoughtful thing someone could do for you? How to impress them.
  11. How can you tell if someone is falling for you? Another chance for them to hint.
  12. What do you find sexiest about a potential partner? Flattering and flirty.
  13. Have you ever had a crush on a friend? See if you have potential.
  14. What are three words you’d use to describe your perfect partner? Compatibility clues.
  15. Do you believe there’s a difference between having chemistry and compatibility with someone? Insight into what they prioritize.
  16. Where would you go if you wanted to have a romantic, secluded getaway with someone special? Dreamy trip planning.
  17. How do you know if a potential relationship is worth pursuing? Look for hints about you.
  18. Who’s your celebrity crush and why? Reveals their “type” playfully.
  19. Do you think relationships take effort or should feel easy? How to approach dating them.
  20. How do you feel about public displays of affection? Good to know if you date.

10 Questions to Ask Your Crush to Get to Know Them Better

10 Questions to Ask Your Crush to Get to Know Them Better

If your crush seems receptive to flirting, you can gradually get more personal with questions that reveal their interests, values, and life experiences. This builds intimacy while showing you want to know them as a whole person. Here are 10 examples:

  1. What’s your biggest goal in life right now? Hopes, dreams, and ambition are revealing.
  2. What do you value most in a friendship? Shows what they want in a relationship too.
  3. When have you felt most proud of yourself? Moving life stories build bonds.
  4. What’s your biggest pet peeve? Knowing annoying things to avoid is useful!
  5. Where is the most interesting place you’ve traveled to? Wanderlust and adventure are attractive.
  6. What’s important to you that you look for in a partner? How to show you have these qualities.
  7. How do you like to be cared for when you’re sick? Thoughtful and caring.
  8. What’s the most thoughtful gift you’ve ever received? Gift ideas for them.
  9. What’s your top priority for the next 5 years? Hopes, dreams, and compatibility clues.
  10. What do you do when you need to de-stress? Compatibility and caretaking.

5 Flirty Questions that Hint You Want More

Once you have rapport with your crush and know you’re compatible, you can get even bolder with flirty questions that signal you’re interested in them romantically. A bit of intimacy and innuendo can start turning things from friendship toward dating. Some examples:

  1. What’s your favorite body part on a potential partner? Let them describe their “type.”
  2. Have you ever fantasized about someone you know? They may admit it’s you!
  3. What’s something you find irresistible in a crush? How to attract them.
  4. If we went on a romantic vacation together, where would we go? Paint a dating fantasy.
  5. What are some ways someone could get your attention if they liked you? Apply this to win them over!

5 Cute Questions to Ask Your Crush

5 Cute Questions to Ask Your Crush

After hinting at romance, pulling back with some cute questions can relieve pressure and make your crush smile. These show you still want to take the time to simply get to know them better in a lighthearted way:

  1. What did you want to be when you grew up? Get to know their childhood dreams.
  2. Do you have any funny family stories from when you were younger? Bond over families.
  3. Do you have any nicknames? How did you get them? Playful personal history.
  4. What toys or games did you love as a kid? Nostalgia is bonding.
  5. Do you have any secret talents? Quirky and intriguing.

5 Deep Questions to Ask Your Crush

5 Deep Questions to Ask Your Crush

Deeper questions can strengthen emotional intimacy, but only ask them if you already have a strong connection established. Vulnerability and sharing fears requires trust built over time. Some examples:

  1. What’s something you’re afraid of that you’d only admit to someone you really trust? Say this exact line, then share a fear first to show you’re opening up too.
  2. Is there anything missing in your life right now that you really want? They may say romance or reveal relationship goals.
  3. What’s one thing you want to accomplish or experience before you die? Hopes and dreams reveal character.
  4. What are some difficult lessons life has taught you so far? Building empathy.
  5. Is there anything you wish you could change about yourself? Insecurity can bind you.

5 Serious Questions to Ask Your Crush

5 Serious Questions to Ask Your Crush

If things seem to be heading toward an exclusive relationship, you can ask more serious questions to discuss big topics to see if you’re on the same page about the future. Some examples:

  1. Do you want marriage, or are you happy just dating? Gets at long-term goals.
  2. Do you want kids someday? Essential compatibility question if you’re serious.
  3. How many kids do you see yourself having? Again, need to agree here if really serious.
  4. Where are some places you’d like to live someday? Discuss future dreams.
  5. What spiritual beliefs or values are important to you? Core compatibility factor.

5 Questions to Ask Your Crush About Their Past

5 Questions to Ask Your Crush About Their Past

As you share more of your lives, you may gently ask about past relationships, but don’t push it. Focus on who they are now versus digging into potentially hurtful history. Some examples:

  1. What’s the longest relationship you’ve had? Gives realistic relationship expectations.
  2. Have you ever gotten back together with an ex? Some do, some don’t.
  3. What’s something that ended a past relationship? Incompatibility clues.
  4. What’s something you learned from a past breakup? Emotional maturity.
  5. What’s something you’d do differently in your next relationship? Shows growth.

5 Questions to Ask Your Crush About the Future

5 Questions to Ask Your Crush About the Future

Hopeful questions about the future, even before you’re officially dating, can open the door to imagining a relationship with you. But don’t go overboard too fast:

  1. Where do you see yourself in 5 years? Share your compatible vision too.
  2. What are your top goals and priorities for the next few years? Align your dreams.
  3. Where do you see yourself living in the future? Discuss compatibility.
  4. What’s on your bucket list for travel? Plan dream trips together.
  5. What do you look forward to most in the next year? Compatibility clues.

5 Conversation Starters for When You First Text Your Crush

When you get your crush’s number, keep your first text simple yet engaging. Fun questions and observations get a convo flowing naturally so you can gradually flirt more later. Some examples:

  1. Hey! It was really nice talking with you the other day at [location]. How’s your week going so far?
  2. Hey [their name]! This is [your name] from [context where you met]. I just found this cool article on [topic you discussed] and thought you might like it too. How’s your day going?
  3. Hi! It’s [your name]. You mentioned [something they said] when we met, so I thought I’d share this funny meme about [that topic]. What’s up?
  4. Hey, I was just listening to [song/artist/genre they said they liked] and thought of you! How’s it going?
  5. Hi [their name]! [Make an observation about something they shared or compliment them]. Any fun plans for this weekend?

Conversation Starters to Text Your Crush After the First Date

5 Conversation Starters for When You First Text Your Crush

If your first date went well, keep things light and friendly instead of overly flirty or pushy right away. Give a genuine compliment and continue getting to know their interests. Some examples:

  1. I had a really great time with you last night! Thanks for being such wonderful company.
  2. That restaurant we went to was so good! I’ll have to try [dish they recommended] next time. What kinds of food do you like cooking at home?
  3. You have such an awesome sense of humor. I was laughing all night! What comedies have you seen lately that I should add to my watchlist?
  4. It was cool hearing about your travel adventures in [place they mentioned]. Where’s another trip on your bucket list? Someday I’d love to go to [place you want to visit].
  5. Thanks again for going out with me last night. I hope we can do it again sometime! I was thinking maybe we could [simple second date idea] next? Let me know if you’re free!

Questions to Text Your Crush if You Haven’t Seen Them Lately

Questions to Text Your Crush if You Haven’t Seen Them Lately

If communication has stalled with someone you like, reopen the door in a warm, interested (but not desperate) way. Bring up something they responded well to before. Some examples:

  1. Hey! Haven’t heard from you in a bit, so I just wanted to say hi. I was watching [show you talked about before] the other day and it made me think of our conversation about [topic reference]. How have you been?
  2. Hi [their name], I hope you’ve been well! I came across this funny [reference they’d find amusing] today and thought of you. What have you been up to lately? Would love to catch up soon!
  3. Long time no chat! I was just listening to [musician they like] and I remembered how much you enjoyed them too. What kinds of new music have you been into lately? Would be great to talk soon!
  4. Happy [upcoming holiday/event reference]! I know you mentioned [relevant detail] was one of your favorites. Any big plans to celebrate? I’d love to hear what you’ve been up to lately! Hope you’re doing great.
  5. Hey stranger! Just wanted to check in and say hi since we haven’t chatted in a bit. Let me know how you’re doing and if you’d like to get coffee sometime to catch up! I’d love to hear what you’ve been up to.

Key Takeaways: Flirty yet Thoughtful Texts to Get Closer to Your Crush

  • Break the ice with playful questions about favorites, hobbies, travel goals, and hypotheticals
  • Ask “would you rather” questions to spark fun debates and get compatibility clues
  • Gradually hint your interest with sweet, romantic questions once you have rapport
  • Get to know them better emotionally with thoughtful, personal questions
  • If your crush reciprocates interest, you can get a little flirty and suggestive
  • Cute questions provide an intimate touch without being too intense
  • Deep questions strengthen bonds if you already have established trust
  • Serious questions assess long-term alignment if you’re exclusive
  • Gentle questions about past relationships provide insight at the right stage
  • Discuss future plans together if things are progressing romantically

Texting a crush can feel like a balancing act – you want to keep things light and fun, but also gradually get deeper in order to move the relationship forward. The key is pacing yourself and reading their signals.

If your crush responds positively to flirty or serious questions, take it as a green light to keep exploring that direction. But if they give short replies or change the subject, switch gears to taking things slower.

While texts are a great start, don’t be afraid to speak up if you want more. After some genuine conversations, you could say something like:

“It’s been really nice getting to know you over text – I’d love to keep talking in person sometime too! Let me know if you’d be up for grabbing lunch this weekend.”


Texting your crush opens up an exciting, low-pressure way to break the ice or advance a budding relationship. Start with fun, flirty questions to spark conversation and build rapport. If you notice mutual chemistry, gradually get more personal to reveal your romantic intentions.

Remember to keep showing friendly interest in who they are as a person – not just flirting. Asking thoughtful questions helps nurture emotional intimacy and compatibility. Tread lightly with anything too intense or suggestive until you know your crush is receptive based on their responses.

With the right balance, flirty texts can lead to a great first date, and eventually turn your crush into a real relationship full of chemistry. So take a chance and start texting! You never know what fun connections are waiting when you make the first move to text your crush.

Frequently Asked Questions(FAQs)

Q1: How can I come up with good flirty questions to ask my crush over text?

A: When texting your crush, try asking playful questions like their favorite emoji or music, hypotheticals like “would you rather,” and romantic questions once you have rapport. Flirty yet thoughtful questions like these can help spark conversation, reveal compatibility, and hint at your romantic interest. Just be sure to start slower and gradually build intimacy.

Q2: What kind of flirty questions might be too intense for a new crush?

A: Questions that are too suggestive or intimate too soon, like asking about sexual fantasies or past relationships, can make your crush uncomfortable. Get to know them first with light, friendly questions and don’t take things to a deeper romantic level unless they reciprocate interest over your conversations.

Q3: How can I keep a text conversation going with my crush after we run out of questions?

A: Rather than just asking questions, keep things flowing by telling stories, making amusing observations, and opening up about your own experiences as well. This builds intimacy beyond just interview-style questioning. You can also re-reference earlier conversations and follow up on things they’ve mentioned before.

Q4: What are some cute but flirty questions to ask my crush?

A: Cute flirty questions include asking about their childhood nicknames, favorite toys/games growing up, secret talents, or anything nostalgic and playful. You can also ask hypotheticals like their favorite animal or superpower. These lighthearted questions provide flirty intimacy without being too intense.

Q5: What flirty questions should I avoid when texting my new crush?

A: Avoid overly sexual questions or pushing for details about past relationships too soon. Don’t ask invasive questions just to satisfy curiosity if you don’t know them well yet. Keep things flirty but focused on getting to know their personality when you’re just starting out. If they reciprocate interest, you can gradually get more intimate.

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