200+ Best Questions to Ask Someone You Like (Texting & IRL)

Looking to learn more about your crush and deepen your connection? Asking engaging questions is the best way to bond with someone, whether you’re chatting over text or IRL. In this article, we’re providing the ultimate list of fun, flirty, and interesting questions to ask someone you like. We also talked to dating experts Lauren Sanders and Laura Bilotta for tips to break the ice and show interest in a subtle way.

Flirty Questions to Ask Your Crush

What’s your usual type?
What’s your love language?
What’s your biggest turn-on?
What’s your idea of the perfect date?
Are you interested in anyone right now?
What’s your favorite thing about yourself?
What are your green flags in a relationship?

Section 1 of 11:

Icebreaker Questions

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Ask casual, open-ended questions to get to know your crush better. To avoid sounding like a job interview, rephrase classic icebreakers in an engaging way. Try to form open-ended questions about their personality, hobbies, interests, and tastes, and share your answers after they respond to build trust and intimacy. If you’re texting your crush, you could suggest playing a game of 21 Questions to keep the conversation fun and lighthearted.
- What’s your dream job?
- Where did you grow up?
- What’s your zodiac sign?
- Who’s your favorite artist?
- Who’s your celebrity crush?
- What’s your favorite season?
- What could you write a book on?
- What was your last Netflix binge?
- Are you introverted or extroverted?
- Are you an early bird or a night owl?
- What’s one thing on your bucket list?
- What’s your favorite outdoor activity?
- What’s the best character of all time?
- What does your perfect day look like?
- What song can you never get sick of?
- What’s one thing you can’t live without?
- What are 3 things that make you happy?
- What’s your dream vacation destination?

Section 2 of 11:

Flirty Questions

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Ask flirty questions to create a playful mood and show interest. Looking to spice up the conversation and let your crush know you’re interested? Ask them about their turn-ons, dating history, and relationship preferences to make it clear that you’re attracted to them. Being direct leaves little room for interpretation, and if the conversation goes well, you can suggest a casual date related to something you discussed.
- What’s your toxic trait?
- What gives you the “ick?”
- When was your first kiss?
- What do you wear to bed?
- You know you’re cute, right?
- What’s your biggest turn-on?
- What’s your best pick-up line?
- Do you develop crushes easily?
- Have you ever dreamt about me?
- What song puts you in the mood?
- What do your friends think of me?
- Have you always been this funny?
- What are you doing this weekend?
- Do you think you’re a good kisser?
- What’s your biggest guilty pleasure?
- What’s your favorite thing about me?
- Are you interested in anyone right now?
- What’s the most attractive physical feature?
- If you were me for a day, what would you do?
- What’s something you’ve always wanted to ask me?
- What’s the first thing that comes to mind when you think of me?

Section 3 of 11:

Dirty Questions

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Test the waters with flirty questions before moving onto spicier ones. If you want to take your friendship to the next level, asking your crush suggestive questions is the easiest way to express interest. Just make sure they’re comfortable with spicier subjects before jumping in. If they don’t seem engaged in real life (or responsive over text), apologize and switch to a tamer topic.
- Do you like dirty talk?
- What’s your favorite position?
- What color is your underwear?
- Who’s your celebrity hall pass?
- How do you feel about sexting?
- Are you submissive or dominant?
- Do you prefer giving or receiving?
- Would you ever make a sex tape?
- How often do you think about sex?
- Do you have any kinks or fetishes?
- Fast and fiery, or slow and sensual?
- What’s your biggest sexual fantasy?
- Have you ever fantasized about me?
- What’s your favorite part of my body?
- Have you ever been caught in action?
- Have you ever been turned on at work?
- What’s your favorite place to be kissed?
- How do you feel about one-night stands?
- Do you prefer being on top or bottom?
- What’s the craziest place you’ve had sex?
- Do you prefer loud or silent people in bed?
- Do you prefer morning sex or evening sex?
- What’s your most awkward sexual experience?
- What clothing do you think I look the sexiest in?
- If I was in your room right now, what would you want me to do?

Section 4 of 11:

Romantic Questions

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Ask about their relationship goals to see if you’re compatible in real life. If you want to determine if you’re a good match for your crush, ask them questions about love and dating. Talk about what you both want out of a relationship, how they cope with conflict, and how they prefer to give and receive love. By exploring their values and communication style, you can get to know them better and see if they’re the right person for you.
- Are you a romantic person?
- What’s your love language?
- Have you ever been in love?
- Do you believe in soulmates?
- What does love mean to you?
- What’s your favorite love song?
- Do you prefer kissing or cuddling?
- What’s your favorite memory of us?
- Do you believe in love at first sight?
- Do you feel comfortable around me?
- What's your idea of the perfect date?
- What traits do you look for in a partner?
- How would you describe me in 3 words?
- What’s the best movie to watch on a date?
- What’s something that reminds you of me?
- What are your green flags in a relationship?
- Do you prefer being single or in a relationship?
- If we had a Netflix show, what would it be called?
- What’s something unique that you find attractive?
- What’s the best compliment you’ve ever received?
- If we formed a band, what kind of music would we make?
- Do you prefer grand romantic gestures or small surprises?
- If we had to move to another country, where would we go?
- What’s the most romantic thing you’ve ever done for someone?
- If you could have any superpower to impress a date, what would it be?

Section 5 of 11:

Deep Questions

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Ask personal questions if your crush has just opened up to you. According to Sanders, you should “ask about their life goals and values” to learn more about [your crush].^{[1]
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Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Touching on meaningful topics is the best way to build intimacy in any relationship, but if you’re worried about overstepping boundaries, preface by saying it’s totally fine not to answer. The best time to ask these questions is in a relaxed and private environment, especially after your crush has shared something vulnerable.
- Who’s your hero?
- What brings you joy?
- When did you last cry?
- What’s your greatest fear?
- What’s your top goal in life?
- Are you close with your family?
- When was the last time you cried?
- What are you most grateful for?
- What are you the most proud of?
- What’s your biggest regret in life?
- What’s your definition of success?
- Do you care what people think of you?
- Where do you see yourself in 10 years?
- What’s your favorite childhood memory?
- Do you think money can buy happiness?
- What’s something you’re insecure about?
- What are 3 things you love about yourself?
- How have you changed in the past 5 years?
- What’s something you’ve never told anyone?
- What’s the biggest misconception about you?
- Do you think physical or emotional pain is worse?
- What did you want to be when you were younger?
- What’s one thing you would do if you knew you wouldn’t fail?

Section 6 of 11:

Interesting Questions

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Suggest hypothetical scenarios to save a dying conversation over text. If your conversation is getting a bit boring, ask your crush a creative “what if” style question to reveal more of their personality. You can preface the question by suggesting a fun game or randomly throwing it out there to catch them off guard. Here are some fun options to help you get started:
- If you were invisible for a day, what would you do?
- If you were a mad scientist, what would you invent?
- If you could stop time for a year, what would you do?
- If you could master one skill instantly, what would it be?
- If you could time travel, which decade are you going to?
- If you woke up as an animal, what would you want to be?
- If you could play any instrument, what would you choose?
- If you won the lottery, what’s the first thing you would buy?
- If you could live in any fictional world, where are you going?
- If you could stay one age forever, which would you choose?
- If you could eliminate one historical event, what would it be?
- If the floor was lava, how would you get from place to place?
- If you could make any kid’s TV show, what would it be about?
- If you could solve one problem in the world, what would it be?
- If you could only see one color, what color would you choose?
- If you could guest star on any TV show, what would you choose?
- If you were an Olympic athlete, what sport would you compete in?
- If you were given the death penalty, what would your last meal be?
- If you were born 100 years earlier, what would your occupation be?
- If you could master any language instantly, what would you choose?
- If you could only watch one movie for the rest of your life, what would it be?
- If you could only listen to one artist for the rest of your life, who would you pick?
- If you could create your dream band with 5 artists, dead or alive, who would be in it?
- If someone followed you around and narrated your life, who would you want it to be?
- If you could have an unlimited supply of one thing for the rest of your life, what would you choose?

Section 7 of 11:

Funny Questions

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Throw out a silly question to break tension and make your crush laugh. Sharing a laugh with someone is proven to strengthen relationships.^{[2]
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Trustworthy Source

Greater Good Magazine
Journal published by UC Berkeley's Greater Good Science Center, which uses scientific research to promote happier living

Go to source} So, come up with a goofy question to bond with your crush and get the giggles going. If you’re talking in person, wink, smile, or use a playful tone to enhance your humor. If you’re texting them, incorporate fun emojis to lighten the mood.
- What’s your most useless skill?
- Which Shrek movie is the best?
- What’s your least favorite scent?
- What’s your biggest irrational fear?
- Do you think a hot dog is a sandwich?
- Who’s the most attractive animated character?
- Would you rather be bald or have no eyebrows?
- What’s the best prank you’ve pulled on someone?
- Would you rather always shout or always whisper?
- What’s the most embarrassing thing in your closet?
- What’s the dumbest thing you’ve done while drunk?
- What’s the funniest thing you believed in as a child?
- If animals could talk, which one would be the rudest?
- How long could you survive in a zombie apocalypse?
- If you could fight any historical figure, who would it be?
- Would you rather wear orange Crocs or Big Red Boots?
- What’s the most unnecessary white lie you’ve ever told?
- What’s an embarrassing song or band you secretly love?
- What’s the best excuse you’ve given to skip school or work?
- What’s one inanimate object you would delete from existence?
- What’s the most savage insult you can come up with on the spot?
- When’s the most inappropriate time you've laughed at something?
- What’s the weirdest or most shocking thing you’ve seen in someone’s house?
- Would you rather always feel like you have to sneeze or sneeze 500 times a day?
- What’s the creepiest thing you could say to a stranger when passing them on the street?
- Would you rather talk like Mickey Mouse when you’re angry or turn into the Hulk when you’re turned on?

Section 8 of 11:

Juicy Questions

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Start off with lighter questions before gradually moving onto juicer ones. If you want to put your crush in the hot seat, ask them about their bad habits, embarrassing moments, and anything else that makes them blush. Just make sure to ask these questions in a safe and casual setting, whether it’s in person or over text. You could even share your own thoughts and experiences first to encourage your crush to do the same.
- Do you go on a lot of dates?
- Have you ever broken the law?
- Do you have beef with anyone?
- Have you ever ghosted someone?
- Do you still have feelings for an ex?
- Have you ever gone skinny dipping?
- What’s the most drunk you’ve ever been?
- What’s your hot take or unpopular opinion?
- Would you rather date someone “hot” or “cute?”
- Have you ever spread a rumor about someone?
- Have you ever had a crush on a friend’s sibling?
- What’s the worst way you’ve dumped someone?
- What’s the most embarrassing thing in your room?
- Have you ever sent a dirty text to the wrong person?
- What’s the most scandalous thing you’ve ever done?
- How would you rate your looks on a scale of 1 to 10?
- What’s the worst thing you’ve done at work or school?
- What’s the last thing you searched for on your phone?
- Who’s the last person you’d want to run into on the street?
- What crime would you commit if there were no consequences?
- What’s something you’re glad your mom doesn’t know about you?
- Have you ever let someone take the blame for something you did?
- What’s the dumbest thing you’ve done to get someone’s attention?
- What’s an embarrassing thing you’ve done and never told anyone about?
- Would you rather be more attractive than your partner or have your partner be more attractive than you?

Section 9 of 11:

Questions to Ask While Texting

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Ask open-ended questions to keep the conversation going over text. This prompts more detailed responses from your crush, giving you the opportunity to engage in a back-and-forth exchange. After they answer, share your own response and ask them follow up questions to show you’re interested in what they have to say. You can even incorporate emojis into your text to add a playful touch!
- What’s your life motto?
- What’s your go-to coffee order?
- What emoji reminds you of me?
- What’s your go-to karaoke song?
- Do you believe in fate or free will?
- What’s your favorite place to travel?
- What’s your favorite way to unwind?
- What’s the best meal you’ve ever had?
- What do you think happens when we die?
- What’s the most-used app on your phone?
- What kind of music do you like listening to?
- How do you usually spend your weekends?
- What’s the last thing you purchased for fun?
- What’s something you’re looking forward to?
- What’s the best concert you’ve ever been to?
- What’s the best piece of advice you’ve ever received?
- What’s something you’ve always wanted to learn or try?
- If you could change your name, what would you choose?
- What’s something you wish would go out of style forever?
- What’s the most interesting thing you’ve seen or read this week?

Section 10 of 11:

Questions to Ask to See if They Like You

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Keep the conversation casual to avoid putting pressure on your crush. If you’re trying to determine whether your crush likes you, ask them subtle questions to reveal their feelings and interest level. You could incorporate fake scenarios, hypotheticals, or questions about their past crushes to start a discussion about their feelings. If they don’t seem interested or engaged, just move on to the next topic!
- What’s your usual type?
- Do I make you nervous?
- Do you ever think about me?
- Do you have a crush on anyone?
- When did you last date someone?
- What would our first date look like?
- Do you like spending time with me?
- What was your first impression of me?
- Have you ever had a crush on a friend?
- What do you think we have in common?
- Do you think we have a good connection?
- What do you find most attractive about me?
- Do you like it when other people make the first move?
- What’s your go-to move to impress someone you like?
- How do you show someone that you care about them?
- Have you noticed any changes in our friendship lately?
- Do you think friends can develop feelings for each other?
- Do you think it’s possible for men and women to be friends?
- Do you prefer spending time in groups or one-on-one with someone?
- How do you feel about being friends with someone you’re attracted to?

Section 11 of 11:

Advice on Connecting with Your Crush

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According to Bilotta, some of the top icebreakers are “pets, hobbies, or something that may be relatable to you.” She also says “it’s important to ask open-ended questions that leave room for more than a yes or no answer.”^{[3]
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Expert Source

Laura Bilotta
Dating Coach

Expert Interview} Simply put, find common interests with your crush and ask open-ended questions to keep the conversation going.
To show interest in a subtle way, actively listen to your crush, use open body language when talking to them, and make physical contact from time to time. Pay attention to what they’re saying, ask engaging follow-up questions, and make them feel important and valued.^{[4]
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Research source}
If someone likes you, “they may offer to do nice things for you” or “want to know what’s going on in your life,” according to Sanders.^{[5]
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Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Other signs that your crush may be attracted to you include: acting differently around you, texting or calling you a lot, staring and smiling at you, giving you compliments often, remembering small details about you, and finding excuses to touch or be near you.^{[6]
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Research source}
“Don’t start off by talking about sex,” advises Bilotta.^{[7]
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Expert Source

Laura Bilotta
Dating Coach

Expert Interview} It’s also a good idea to avoid controversial or sensitive topics if you do not know your crush very well. Once your crush feels comfortable around you, however, you may ask more personal questions about their childhood, goals, and beliefs.
According to Sanders, “you have good compatibility if you share common interests, values, and life goals [with them].”^{[8]
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Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Other signs of relationship compatibility include: having strong communication skills with your crush, sharing a similar desire for independence, being physically attracted to one another, sharing similar religious or spiritual beliefs, and matching the same level of extroversion or introversion.^{[9]
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Research source}