Questions That Turn Casual Chats Into Real Talks

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Want to get to know a man without it turning into a full-on grill session? The best questions to ask a guy will keep the flow going without feeling like an interrogation.

As the de facto FashionBeans dating expert, I’ve taken the time to dive into questions that your crush really wants to be asked. Not the corny questions that get thrown out to save a sinking conversation. But the real queries that allow you to dig deeper and connect on a meaningful level… or just questions to have a good laugh.

I asked a handful of men aged between 21 and 45 what some good questions to ask a guy are. You may be surprised at what I found.

Whether you use them in person, over text, or of course, while swiping right, these are the most interesting questions to ask a guy, according to real men themselves.

TL;DR: The best questions to ask a guy are ones that feel natural, open the door to honest answers, and invite deeper conversation without pressure. Aim for curiosity, context, and a tone that encourages genuine sharing.

Key Takeaways

The main thing to remember about good questions to ask a guy is there are a lot of angles you can approach him. If you’re hoping to get to know a guy better, ask him some standard “best of” questions.

As the relationship progresses, you may want to throw in a few serious or flirty questions to bring the conversation to a deeper level. But if you’re just starting to get to know a guy and are trying to play it cool over text, some simple questions will keep the conversation going without getting too heavy.

Let’s break down all the different questions to ask a guy to get to know him deeper, plus real queries to get you started.

Rule of thumb: If a question feels like it can’t be answered in a sentence — and invites elaboration without discomfort — it’s more likely to lead to a meaningful response.

Best Questions to Ask a Guy

The best questions to ask a guy will gently steer the conversation in the right direction. They’ll also help you understand a man better since these questions are designed to get a dialogue going without becoming too deep.

When asking men what constitutes a great question, one of my friends told me, “I like it when I’m asked well thought out questions. Not things like ‘what’s your favorite color.’”

Whip them out on a first date or try them with your partner after a long day at work—these are the best get-to-know-you questions to ask a guy, hands down.

1. What goals are you working towards right now?
2. What’s on your bucket list?
3. How do you relax?
4. Do you enjoy reading?
5. What’s your favorite movie of all time?
6. What food could you eat every day for the rest of your life?
7. What would you do if you won the lottery?
8. What are you most proud of?
9. What’s the scariest thing you’ve ever done?
10. What’s your most watched TV show?
11. Where’s your favorite place you’ve ever been?
12. If you could live anywhere, where would it be?
13. What meal can you cook the best?
14. What are your guilty pleasures?
15. What’s your favorite thing about yourself?
16. Have you ever broken the law?
17. Do you have a lot of friends or a small circle?
18. What’s your dream job?
19. What are your deal breakers in a relationship?
20. What are your pet peeves?
21. How do you spend your weekends?
22. What are some items you can’t live without?
23. What’s your worst habit?
24. Do you collect anything?
25. Have you ever been on a road trip?
26. What are your favorite clothing brands?
27. Do you prefer a city or country lifestyle?
28. What’s your favorite holiday?

Flirty Questions to Ask a Guy

When you’re ready to dial up the heat, these flirty questions to ask a guy to get to know him can get a little spicy. They’re a stellar way to get to know your partner better or to understand a new man that you may be pursuing. The right flirty questions to ask a guy will reveal anything from what he looks for in a companion, information about his past relationships, to his interests in bed.

Just be sure not to whip these out too early since they might be slightly forward first-date material. Though one of my guy friends told me: “I like it when women ask coy questions. I appreciate a woman who is curious and not afraid to ask.”

1. What’s your favorite pickup line?
2. What’s your ideal date night?
3. What’s your biggest turn-on?
4. What’s your love language?
5. Have you ever been in love?
6. What were your past relationships like?
7. Do you believe in love at first sight?
8. What are your hidden fantasies?
9. What’s one thing you’ve always wanted to tell me?
10. Who’s your celebrity crush?
11. What features are you most attracted to?
12. What was your most memorable first date?
13. What do you look for in a romantic partner?
14. How do you like to be woken up in the morning?
15. Do you like to make the first move?
16. What are your feelings about long-distance relationships?
17. Who was your first crush?
18. What’s your favorite position?
19. Have you ever had a threesome?
20. What’s something you’ve always wanted to try in bed?
21. When did you know you were into me?

Funny Questions to Ask a Guy

Knowing how to laugh with someone you’re seeing is an important step in any budding relationship. Whether you’re looking to break the ice or angling for a good giggle, these funny questions to ask a guy will never steer you wrong. They show off your bubbly personality while allowing him to showcase his, too.

Chat through made-up fantasy scenarios, spill silly secrets, and reminisce about ridiculous moments. There’s nothing better for a relationship than having a proper laugh.

1. Who would play you in a movie?
2. What’s your hidden talent?
3. If you were an animal, what would you be?
4. What was your most embarrassing moment?
5. What’s the worst job you’ve ever had?
6. What would your power be if you were a superhero?
7. How would you survive a zombie apocalypse?
8. What’s your go-to joke?
9. What were your favorite cartoons as a kid?
10. Does pineapple belong on pizza?
11. Do you brush your teeth before or after breakfast?
12. If you were a girl for a day, what’s the first thing you would do?
13. What popular foods do you hate?
14. If you could time travel, what year would you go to?
15. What’s your favorite midnight snack?
16. Do you unpack immediately after a trip or let it sit for a few days?
17. What’s the weirdest thing you’ve ever eaten?
18. What three items would you want to have if you were stuck on a desert island?
19. What’s your ultimate comfort meal?
20. What was your best Halloween costume?
21. What was your AIM screenname?
22. What’s one thing you always have in your fridge?

Questions to Ask a Guy Over Text

Trading ‘sups’ back and forth can get boring fast, but these interesting questions to get to know a guy can keep a text conversation exciting. Since you’re talking behind a screen rather than face to face, the dynamic of questions to ask a guy changes.

With more time to choose your words and craft a solid inquiry, there’s no reason not to pull out interesting questions to ask a guy. Plus, my friend Justin told me, “I hate giving live updates about my day, I never respond to ‘what are you doing texts.’ What’s the point? Let’s talk about something real.”

From lighthearted quips to more personal questions to ask a guy, these are the best questions to ask over text (dating apps, included).

1. What was the best part of your day?
2. What’s your favorite emoji?
3. Morning person or night owl?
4. What’s your drink of choice?
5. How do you take your coffee?
6. What did you dream about last night?
7. Who’s your favorite fictional character?
8. What’s your mantra for life?
9. What does your ideal day look like?
10. What made you laugh today?
11. Did you have pets growing up?
12. What’s your favorite quote?
13. What’s your favorite meme?
14. What app do you use most?
15. What’s the coolest photo you’ve ever taken?
16. What’s the weirdest thing that happened to you this week?
17. What foods do you hate?
18. Do you shower in the morning or before bed?
19. What’s your star/zodiac sign?
20. What was your first job?
21. Did you play any sports when you were younger?
22. Are you more of an introvert or extrovert?
23. Can you speak any other languages?
24. Do you have a Type A or Type B personality?
25. What type of music do you enjoy?
26. Do you prefer activity dates or food dates?
27. Are you into sports? What’s your favorite team?
28. Where’s your dream vacation destination?
29. Sun or snow?

Deep Questions to Ask Him

Ready to take things to another level? These personal questions to ask a guy are ideal when you want to dig deeper or if you’re seeking out questions for a new relationship. They tackle some of the trickier topics in life and invite profound thoughts to answer. They also show genuine care on your part since they dive past surface-level niceties, demonstrating you’re ready for the hard conversations and committed to a serious understanding of the other person.

1. Do you believe in soulmates?
2. What’s your most prized possession?
3. What’s your relationship like with your parents?
4. Are you close with your siblings?
5. Are you religious?
6. If you could get one do-over, how would you use it?
7. When was the last time you cried?
8. Do you want to have kids?
9. Do you want a big family someday?
10. What are you most afraid of?
11. Tell me a secret.
12. What would you tell your child self?
13. What’s your favorite childhood memory?
14. Have you ever cheated on someone?
15. Why did your last relationship end?
16. What is your biggest regret?
17. What’s the hardest thing you’ve ever gone through?
18. Who’s your biggest inspiration?
19. What makes you happy?
20. What’s difficult in your life right now?
21. How do you feel the most appreciated?
22. Are you still close with your childhood best friend?
23. What makes you feel safe?
24. What’s the most important thing in your life?

Jane is a seasoned fashion expert with a particular interest in streetwear, accessories, and luxury leather goods. She splits her time between NYC, Paris, and New Zealand, constantly on the hunt for today’s latest trends