Anyone who has ever been on a date — let alone attempted to flirt — can tell you the same thing: It’s hard to know what to say to someone you like. You want to know all these things about them, and as soon as you’re face to face, all coherent thoughts have left your head completely. The same thing can happen over text or when messaging on dating apps.
The key is to have some creative questions to ask a guy tucked in your back pocket. Better than simple statements that do nothing to advance the conversation, questions create room for a thought-provoking back and forth. They can also make it very clear that you’re flirting while providing an easy way for the guy to respond without feeling flustered. (Hey, we all get that way.)
Maybe you go with something relaxed and funny like, “What celebrity would you like to switch places with?” Or you can get personal and learn more about the real him with a question like “How do you hope people will remember you?”
There’s also the option to be as flirty as possible, especially if you’re in the pre-dating zone and want to show a guy you’re interested in exploring things. Try something like, “What would our first date look like?” or the more explicit question, “Have you ever fantasized about me?”
Whatever your mood, you’ll have lots of choices with the ideas below. Here are some of our favorite questions to ask a guy to get to know him.
Fun questions to ask a guy
- Would you rather have a month-long staycation or a week-long adventure?
- If you could meet any one of your heroes, which one would you choose?
- What would your last meal be?
- What meal could you eat every day?
- What fictional character do you wish was real?
- What celebrity would you like to switch places with?
- What superpower do you wish you had?
- What’s the worst movie you’ve ever seen?
- Which movie villain do you think is most misunderstood?
- Which skill would you choose if you knew you could master it in a year?
- What does your ideal Sunday look like?
- What’s your favorite animal?
- Do you drink tea or coffee?
- What’s the craziest thing you’ve ever seen?
- Who would you want to narrate a book about your life?
- What’s your most unexpected talent?
- What’s your favorite movie?
- What position do you sleep in?
- What form of potato is best?
- What’s your favorite item in your closet?
- Are you a morning person or a night owl?
- What’s your favorite holiday?
- If you could be any animal, which one would you be?
- What is the best invention of all time?
- What’s the best costume you’ve ever worn for Halloween?
- How many alarms do you set in the morning?
- Chocolate or candy?
- Mustard or ketchup?
- What’s something illegal that you think should be legal?
- What’s something you would never splurge on?
- What would you be doing if money wasn’t a concern?
- What did you want your job to be when you were a kid?
- Would you adopt a dog or cat?
- Do you remember your dreams?
- What’s something you look forward to every year?
- What’s your go-to meal to make?
- What is the best pizza topping?
- If you had to pick one song to listen to on repeat, what would it be?
- What would be the worst — and most unexpected — animal for you to be trapped in a room with?
- What’s the best trip you’ve ever taken?
- Would you rather it always be cold or hot?
- What’s the best concert you’ve ever attended?
Flirty questions to ask a guy
- What do you find most attractive about me?
- What would our first date look like?
- What are you like as a boyfriend?
- What’s your love language?
- When are you going to ask me out?
- When was the last time you felt butterflies?
- What does love mean to you?
- What’s the worst pick-up line ever?
- Have you ever fantasized about me?
- What would you want to happen if we were alone together right now?
- What’s on your sexual bucket list?
- What’s your wildest sex story?
- What would you cook me for dinner?
- Do you have a type?
- What do you like most about me?
- Do you have any go-to flirting techniques or moves?
- Do you consider yourself romantic?
- Where do you think the most romantic vacation would be?
- Do you like it when a girl makes the first move?
- What’s your favorite sex position?
- What do you find to be the sexiest part of a person’s body?
- What do you tell someone when you want to impress them?
- If you could ask me anything what would it be?
Personal questions to ask a guy
- What’s the longest relationship you’ve ever had?
- Do you believe in soul mates?
- What’s your biggest fear?
- What’s the most useless advice you’ve ever gotten?
- What’s your favorite memory?
- What do you do every night before bed?
- What does being a man mean to you?
- What’s the best date you’ve ever been on?
- What’s the worst date you’ve ever been on?
- What is your biggest dating dealbreaker?
- What’s the scariest thing you’ve ever done?
- Where is your happy place?
- How do you hope people will remember you?
- What does self-care look like for you?
- When was the last time you cried?
- Do you want kids?
- Do you have any regrets?
- What is something you think everyone should experience at least once in their life?
- What is something everyone always gets wrong about you?
- Is there anything you would change about your childhood?
- Where or when do you feel safest?
- How did you meet your best friend?
- What makes you smile on a bad day?
- Would you ever stay friends with an ex?
- Do you want to be more or less like your parents?
- How would you describe yourself in three words?
- What’s the biggest life lesson you’ve learned so far?
- What’s the nicest thing anyone has ever done for you?
- What’s your favorite quality about yourself?
- How old were you when you had your first kiss?
- Who is your favorite family member?
- Are you more of an introvert or an extrovert?
- What’s a question you wish more people asked you?
- What book has stuck with you the longest?
- What’s the meaning of life?
- What age has been your favorite so far?
- What song always hits you in the feels?
- Have you ever been betrayed by a friend?
- Who would you call in an emergency?
