Icebreaker Questions
Ask casual, open-ended questions to get to know your crush. To avoid sounding like a job interview, rephrase classic icebreakers in an engaging way. Form open-ended questions that help you learn more about your crush, while keeping the conversation fun and lighthearted. Some topics you can ask about include their personality, hobbies, interests, and tastes: 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’s your go-to coffee order? 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? What’s the most-used app on your phone? How do you usually spend your weekends? What’s something you’re looking forward to? What’s the best concert you’ve ever been to? What’s something you’ve always wanted to learn or try? What’s the most interesting thing you’ve seen or read this week?
Flirty Questions
Show interest in your crush by asking them a fun and flirty question. Looking to spice up the conversation and let your crush know you’re into them? Ask flirty questions to reveal your feelings in a subtle way! Discover their turn-ons, usual type, and anything else you’ve been dying to know—it’s the perfect way to see if they like you back! What’s your toxic trait? What’s your usual type? Do I make you nervous? 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? What was your first impression of 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? Do you like it when other people make the first move? What’s the first thing that comes to mind when you think of me?
Dirty Questions
Get your crush hot and bothered with these suggestive questions. If you want to turn them on and take things to the next level, shift your questions from flirty to dirty! Just make sure your crush is on the same page as you, and don’t pressure them into answering if they feel uncomfortable. When in doubt, apologize and move on 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 on 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?
Romantic Questions
Ask about their relationship history and goals to see if you’re compatible. If you want to express interest in your crush (and determine if you’re a good match), ask them questions about love and dating. While you should avoid opening up the conversation with these questions, you can work them in later on to see if you share the same values: 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?
Deep Questions
Ask personal questions to connect with your crush on a deeper level. According to matchmaker and dating coach Lauren Sanders, you should “ask them about their life goals and values” to learn more about them. 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 okay not to answer if they feel uncomfortable. 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’s 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? Do you believe in fate or free will? What’s your definition of success? What’s your favorite way to unwind? 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 the best piece of advice you’ve ever received? What’s one thing you would do if you knew you wouldn’t fail?
Interesting Questions
Suggest hypothetical scenarios to take the conversation to the next level. If you want to leave a lasting impression, ask your crush a creative “what if” style question. It’s a great way to catch them off guard, reveal more of their personality, and prompt an unforgettable discussion! 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?
Funny Questions
Throw out a silly question to break the ice and make your crush laugh. Sharing a laugh with someone is proven to strengthen relationships. So, come up with a goofy question to bond with your crush and show off your sense of humor. Whether it’s a wacky hypothetical question or one about their most embarrassing moment, these examples are sure to get the giggles going: 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?
Juicy Questions
Put your crush in the hot seat with these scandalous questions. If you want to get closer to your crush, ask them about their bad habits, embarrassing moments, and anything else that makes them blush. It’s an easy way to deepen your bond without expressing interest in an obvious way. 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?
Frequently Asked Questions
What’s the best way to start a conversation with my crush? According to dating coach and matchmaker Laura 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.” Simply put, find common interests with your crush and ask open-ended questions to keep the conversation going.
How can I express interest in my crush without being obvious? 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.
What are some signs that my crush is interested in me? 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. 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.
Are there any topics I should avoid talking about with my crush? “Don’t start off by talking about sex,” advises Bilotta. 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.
How do I know if my crush is a good match for me? According to Sanders, “you have good compatibility if you share common interests, values, and life goals [with them].” 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.
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