150+ Things to Talk About With Your Crush: Deep, Flirty, & Funny Topics

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Initiate a killer conversation with these creative conversation starters

Co-authored by Judith Gottesman, MSW and Bailey Cho

Last Updated: August 26, 2025 References

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Are you looking for the perfect opening line to talk to your crush and spark a lively discussion? Asking fun and flirty questions is a great way to break the ice and connect with them on a deeper level. Whether you’re chatting in person or over text, here’s the ultimate list of conversation starters to bond with your crush and hint that you’re into them.

1

Get to Know You

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Ask your crush some classic questions to start an effortless conversation. Are you struggling to start a good conversation? Find out basic details about your crush to break the ice and get to know them better. It’s the perfect way to ease into a deeper discussion and see if you have anything in common!^{[1]
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- What’s your dream job?
- Do you collect anything?
- What’s your zodiac sign?
- Do you believe in conspiracies?
- What’s your biggest pet peeve?
- Do you have any hidden talents?
- What could you write a book over?
- Are you an early bird or a night owl?
- Do you have any unpopular opinions?
- What’s the #1 thing on your bucket list?
- What do you like to do in your free time?
- What would you do if you won the lottery?
- What’s your Meyers-Briggs personality type?
- How would you describe your perfect weekend?
- What kind of music have you been listening to lately?

2

Favorites

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Discuss your crush’s favorite things to bond with them. If you want to connect with your crush on a deeper level, find things you share in common. Ask questions about their favorite activities, music, movies, food, and anything else you’ve been dying to know, and chime in when you can relate to their answers. By finding points of connection with your crush, you set the stage for a genuine conversation that doesn’t feel forced or awkward.^{[2]
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Judith Gottesman, MSW
Matchmaker & Dating Coach

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- What’s your favorite band?
- What’s your favorite book?
- What’s your favorite meal?
- What’s your favorite drink?
- What’s your favorite quote?
- What’s your favorite sport?
- What’s your favorite scent?
- What’s your favorite season?
- What’s your favorite dessert?
- What’s your favorite character?
- What’s your favorite vacation spot?
- What’s your favorite way to unwind?
- What’s your favorite day of the week?
- What’s your favorite food combination?
- What’s your favorite YouTube channel?
- What’s your favorite thing to do on a rainy day?

3

Funny

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Get the laughs going with some silly and surprising questions. Looking for ways to make your crush laugh out loud? Bring up something weird, wacky, or straight up silly to start a lighthearted conversation. Sharing a laugh is the best way to bond with someone and strengthen your relationship, whether you’re speaking to them in person or over text.^{[3]
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- What gives you the ick?
- Is a hot dog a sandwich?
- What’s your most useless skill?
- Which Shrek movie is the best?
- What movie scarred you as a kid?
- What’s your biggest irrational fear?
- What’s your favorite form of potato?
- Have you ever re-gifted something?
- How many holes does a straw have?
- Which meme best represents your life?
- What’s the best Wi-Fi name you’ve seen?
- What’s the worst date you've ever been on?
- What’s an embarrassing song you secretly love?
- What’s the longest you’ve gone without showering?
- Would you rather have no eyebrows or no eyelashes?
- What’s the most unnecessary white lie you’ve ever told?
- Reader Poll: We asked 3488 wikiHow readers and 49% of them agreed that their favorite way to break the ice is by asking funny or silly questions [Take Poll]. So, these wacky questions are certain to help you get the convo started with your crush!

4

This or That

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Hit them with some rapid fire questions to revive a dull discussion. Did the last conversation with your crush die out quickly, or did you find it a little dry or awkward? Use these quick and easy questions to make up for your last exchange and spark a flirty debate. To keep the conversation going, ask your crush why they chose their answer, or tease them if you have a different opinion.
- Beach or mountains?
- Tea or coffee?
- Fruit or vegetables?
- TV show or movie?
- Past or future?
- Dine in or take out?
- Instagram or TikTok?
- Twitch or YouTube?
- Cats or dogs?
- Summer or winter?
- Text or call?
- Fiction or nonfiction?
- Sleep or binge-watch?
- Introvert or extrovert?
- Playlists or podcasts?

5

Creative

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Suggest hypothetical scenarios to take the conversation to the next level. If you want to catch your crush off guard (and really pick their brain), come up with a unique “what if” or “would you rather” question about the past, present, or future. It’s a foolproof way to find out about their personality and prompt a lively discussion.^{[4]
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- If you were president for one day, what would you do?
- If you could fight any historical figure, who would it be?
- If you could live in any fictional world, where are you going?
- If you could master one skill instantly, what would you choose?
- If you could stay one age forever, what age would you choose?
- If you were born 100 years earlier, what would your occupation be?
- If you could only eat one meal for the rest of your life, what would it be?
- Would you rather explore space or the deep sea?
- Would you rather run at 100 MPH or fly at 20 MPH?
- Would you have a personal maid or a personal chef?
- Would you rather never sleep again or never eat again?
- Would you rather be chronically overdressed or under-dressed?
- Would you rather have a pause button or a rewind button in your life?
- Would you rather always have a full phone battery or a full tank of gas?
- Would you rather be fluent in every language or be able to speak to animals?

6

Flirty

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Show your crush you’re into them with some fun and flirty questions. Trying to spice up the conversation and let your crush know you’re interested? Ask bold, suggestive questions to make them blush (and get them all hot and bothered). By flirting with your crush, you can communicate your attraction and take your relationship to the next level.^{[5]
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- Am I your type?
- What do you wear to sleep?
- What’s your biggest turn-on?
- Who’s your celebrity hall pass?
- What song puts you in the mood?
- Do you think you’re a good kisser?
- What was your sexual awakening?
- Have you ever gone skinny dipping?
- Have you ever fantasized about me?
- What was your first impression of me?
- Where would you take me on our first date?
- What’s something non-sexual that turns you on?
- Do you prefer being the big spoon or little spoon?
- Do you prefer other people to make the first move?
- How do you know when you have a crush on someone?

7

Family & Upbringing

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Connect with your crush on a deeper level by asking about their family. If you’ve known your crush for a while, feel free to ask about their family life to get to know them better. Just be sure you bring up the topic in a gentle and respectful way, and ask your questions with a positive twist. For example, instead of directly asking if they have a good relationship with their parents, you might ask, “Who are you closest to in your family?”^{[6]
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- How many siblings do you have?
- Who’s your favorite family member?
- Are you more like your mom or dad?
- What makes you feel most at home?
- Are you close to your extended family?
- What are your favorite family traditions?
- Did you grow up in a religious household?
- What’s the coolest thing about your family?
- How often do you hang out with your parents?
- Do you consider your parents to be your friends?
- What does your family like to do during vacations?
- Who did you compare yourself to the most growing up?
- Which family member do you turn to when you need help?
- What’s the most important thing you’ve learned from your family?

8

Childhood

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Take a trip down memory lane to prompt an engaging conversation. If you want to remind your crush of the good old days (and connect with them on a deeper level), ask about their childhood to bring up feelings of nostalgia. To keep the conversation light, focus on their interests, hobbies, and school life, and be sure to point out similarities if you share any experiences.^{[7]
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Expert Source

Judith Gottesman, MSW
Matchmaker & Dating Coach

Expert Interview}
- What kind of student were you?
- What was your dream job as a child?
- What’s the first concert you attended?
- What’s your favorite childhood memory?
- What were you most afraid of as a child?
- What was your favorite series as a child?
- What was your favorite subject in school?
- Did you have imaginary friends growing up?
- What was your favorite TV show growing up?
- What do you miss the most about childhood?
- Did you have any silly nicknames growing up?
- What was your most prized possession as a child?
- What’s the funniest thing you believed in as a child?
- What extracurricular activities did you join in school?
- How did you usually spend summer break as a child?

9

Deep

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Delve into personal questions to deepen your relationship. If you feel comfortable with your crush, don’t be afraid to bring up more serious topics like their dreams, goals, and fears. Talking to them about these things lets them know you care about them, and it can strengthen your emotional connection.^{[8]
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- Who’s your role model?
- What’s your greatest fear?
- When’s the last time you cried?
- What are you the most grateful for?
- What are 3 things you can work on?
- What do you love most about yourself?
- What gets you out of bed in the morning?
- What do you want to be remembered for?
- Do you care what other people think of you?
- What would you do if money were no object?
- Which is worse: physical pain or emotional pain?
- What’s something no one else knows about you?
- What’s the biggest life lesson you’ve learned so far?
- What’s the biggest misconception people have of you?
- What’s the most challenging part of your life right now?

10

Philosophical

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Throw in a thought-provoking question to catch your crush off guard. When you’re in the mood for a “rabbit hole” discussion, ask your crush about human nature, happiness, ethics, death, and spirituality.^{[9]
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- Is war ever justifiable?
- Is ignorance really bliss?
- Is it wrong to kill animals?
- Why do people fear death?
- What happens when we die?
- What does it mean to be happy?
- Do you believe in fate or free will?
- What determines success vs. failure?
- Do you believe in capital punishment?
- What’s more important: love or money?
- What would happen if we lived forever?
- Would you kill 10 people to save 1,000?
- Is there anything wrong with being selfish?
- Can we choose our emotions or do they just happen?
- Is the most important purpose in life to find happiness?

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