Flirty, Deep & Fun Questions to Ask a Guy or Girl Over Text

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How to start a conversation and show them you’re interested

Co-authored by John Keegan and Aly Rusciano

Last Updated: January 22, 2025 Fact Checked

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• Flirty Questions
|
• Personal Qs
|
• Deep Qs
|
• Fun Qs
|
• Expert Advice on Crushes
|
• Video
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• Tips

|Show more |Show less

You open your phone to text your crush. Your fingertips hover over the keyboard…Gah! What do you even say? We get it. Texting your crush can be nerve-wracking, but you’ve got this! There are plenty of things you can ask them to start a conversation. We talked to relationship and dating experts to give you the best advice, so take a look at the list of questions below for some inspiration (you can even copy and paste—we won’t tell).

Steps

Section 1 of 5:

Flirty Questions

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1. 
   Spice things up with a cute question that shows your interest. Test the waters and gauge if they like you back by asking them a cute or risque question. Flirting through text is an excellent way to put yourself out there without risking public embarrassment. If they’re interested, great! If not, you can simply change the subject. Try sending your crush one of these flirty or romantic questions to see how they feel:

   • What makes a perfect date?
   • What does your dream date night look like?
   • What was your first kiss like?
   • Who’s your celebrity crush?
   • What’s your best pick-up line?
   • What emoji reminds me of you?
   • What do your friends think of me?
   • Do you think you’re a good kisser?
   • What was your first impression of me?
   • What do you think we have in common?
   • What do you like most about me?
   • Do you like it when other people make the first move?
   • What are your biggest turn-ons?
   • What do your friends know about me?
   • Have you ever dreamt about me?
   • Are you interested in anyone right now?
   • Do I make you nervous?
   • What are you doing this weekend?
   • Do you like to cuddle?
   • What do you wear to bed?
   • Has anyone ever told you how nice your hair is?
   • Why are you so cute?
   • Are you a top or bottom?
   • What was your first time like?
   • What’s your favorite body part?
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Section 2 of 5:

Personal Questions

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1. 
   Get to know your crush by asking them about their life. Strike up a conversation and show you’re interested by asking about their hobbies, interests, and favorite things. With over 10 years of experience helping couples, relationship expert Joshua Pompey recommends avoiding the small talk and getting into the more personal questions right away. Think about things you want to know about them and go for it! Here are some examples:

   • Where did you grow up?
   • Do you have any siblings?
   • Do you have any pets?
   • What do you like to do on the weekends for fun?
   • What do you do for a living?
   • What’s your zodiac sign?
   • Are you a morning person or a night owl?
   • What’s your favorite joke?
   • What’s your favorite movie?
   • What’s your favorite reality TV show?
   • Who’s your favorite artist?
   • What’s your favorite food?
   • Who’s your favorite author?
   • What did you do this past weekend?
   • Do you prefer to call or text?
   • What’s something you’re proud of?
   • What song can you never get sick of?
   • What’s something you’re looking forward to?
   • What was your first social media username?
   • What does your “perfect” day look like?
   • What’s your dream job?
   • What’s on your bucket list?
   • What’s one place you want to travel to?
   • What’s the most memorable place you’ve been?
   • What’s the first movie you saw in theaters?
   • What kind of music do you like listening to?
   • What’s one thing you can’t live without?

Section 3 of 5:

Deep Questions

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1. 
   Learn something new about them by asking about their inner thoughts. If you want to get to know your crush even more, don’t hesitate to send them a text with a more serious question. While you don’t want to pry, it’s totally cool to ask their opinion on certain things or dig below surface level (especially if you’re hoping to go out with them). For instance:

   • What’s your favorite childhood memory?
   • What’s the best compliment you’ve ever received?
   • Are you close to your parents?
   • What’s your favorite quality in a person?
   • What do you value most in a person?
   • How did your last relationship end?
   • Have you ever been in love?
   • What are you passionate about?
   • What’s the best gift you’ve ever received?
   • Have you ever been to therapy?
   • Would you ever want to be famous?
   • What’s your earliest memory?
   • What are your pet peeves?
   • Do you believe in soulmates?
   • What’s your love language?
   • What do you want to do differently in your next relationship?
   • What’s the worst lie you've ever told?
   • What’s the hardest thing you’ve ever had to do?
   • What’s your biggest fear?
   • What’s your most embarrassing memory?
   • What are your relationship red flags?
   • Who do you look up to the most?
   • What’s something you’d like to learn more about?
   • What’s the most important lesson you’ve learned?
   • What are your life goals?
   • Are you religious?
   • How do you approach and react to conflict?
   • How do you cope when you’re stressed or worried?
   • What’s your attachment style?
   • What do you think happens when you die?
   • What do you like most about yourself?
   • What’s the best and worst thing about dating?
   • Do you want to have kids someday?
   • What do you want to be remembered for?
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Section 4 of 5:

Fun Questions

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1. 
   Keep the conversation light-hearted with a silly question. Play a game of Would You Rather, 21 Questions, or This or That. Not only is this a great way to have fun with your crush via text, but it can also help you get to know them better! Dating coach John Keegan recommends “keeping the text message light, keep it fun.” Give some of these silly and interesting questions a try:

   • How would you prepare for a zombie apocalypse?
   • If you had a superpower, what would it be?
   • Who would you want to play in a movie?
   • If you could meet someone famous, who would you meet?
   • Would you rather be a duck or a chicken?
   • Would you rather order an appetizer or a dessert?
   • Do you prefer breakfast, lunch, or dinner?
   • What’s your ideal sandwich?
   • If you were an animal, what animal would you be?
   • What would you change if you could go back in time?
   • What’s the best fun fact you know?
   • What’s your go-to karaoke song?
   • Do you prefer a sweet or savory breakfast?
   • What’s the last thing you purchased for fun?
   • Do you shower in the morning or at night?

Section 5 of 5:

Expert Advice on Crushes

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1. 
   We talked to some of the best relationship and dating experts around to bring you the best advice. Check out their tips for getting to know your crush or making a move via text:

   • Personalize the questions you send your crush. As John Keegan says, “The number one way to show someone that you like them is to pay attention to them.”
   • Dating coach Imad Jbara warns that everyone has their own texting style, so be aware that your crush may take a question differently than you, and that’s okay!
   • Keegan says that your crush is probably into you if they interact with your messages, respond regularly, and initiate conversations.
   • Dating and relationship coach Mark Rosenfeld recommends using emojis when flirting with someone via text. A 😉 or 😚 helps show that you’re being more than friendly.
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Tips

• Ask open-ended questions that need a more thorough response than “yes” or “no.” This way, you can keep the conversation going.
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