140 How Well Do You Know Me Questions for Every Kind of Bond

How well do you know me questions are more than just trivia about someone’s favorite color or dream vacation—they’re a way to feel seen. Whether you’re asking these questions to a best friend, partner, sibling, or even throwing them into a group chat for fun, they reveal the tiny details, inside jokes, and deeper thoughts that define connection. Some will be easy, others might stump even your closest person, but all of them are designed to get you thinking, laughing, and talking.

Easy and Everyday

These are the basics—but don’t underestimate them. Even simple questions can reveal surprising gaps (or strengths) in how well someone really knows you. Start here to warm up the conversation or test how much your person’s been paying attention.

1. What’s my favorite color?

2. Do I prefer coffee or tea?

3. What time do I usually wake up?

4. What’s my go-to comfort food?

5. Am I more of a morning or night person?

6. What’s my favorite season?

7. Do I like sweet or salty snacks more?

8. What’s my favorite thing to watch when I’m sick?

9. What’s my most-used emoji?

10. What’s one thing I always carry with me?

11. Do I prefer books or movies?

12. What’s my favorite app?

13. What’s my dream vacation spot?

14. Do I like spicy food?

15. Am I more into dogs or cats?

16. What’s my usual order at a fast food place?

17. What’s my favorite holiday?

18. Do I sing in the shower?

19. What’s my favorite genre of music?

20. Do I like mornings quiet or with music?

Funny and Slightly Weird

This is where things get silly. These weird and offbeat questions are great for shaking off awkwardness and seeing who really understands your quirks. Laughter is guaranteed—and so are a few head-tilting surprises.

1. If I were a cereal, which one would I be?
2. What weird food combo do I actually love?
3. What’s the most embarrassing thing I’ve ever done (that I’ve told you)?
4. Would I survive a zombie apocalypse?
5. What’s my guilty-pleasure song?
6. If I were a fictional character, who would I be?
7. What animal do I act like when I’m tired?
8. Do I have a conspiracy theory I believe in (even just a little)?
9. What’s the weirdest dream I’ve told you about?
10. What word do I overuse?
11. What’s something I’d never do—even for a million dollars?
12. What’s the weirdest compliment I’ve ever received?
13. If I had a signature dance move, what would it be?
14. What food do I irrationally hate?
15. What would I name my pet dragon?
16. If I could teleport anywhere right now, where would I go?
17. What would my pirate name be?
18. What’s my most chaotic trait?
19. What would I bring to a desert island that makes zero survival sense?
20. What’s something about me that seems fake but is true?

Personal and Reflective

If you want to go deeper, this is the zone. These questions aren’t about facts—they’re about feelings, memories, and inner worlds. Perfect for close friends, late-night talks, or anyone who wants to be seen beneath the surface.

1. What’s something I’m secretly proud of?
2. What’s a memory I talk about a lot?
3. What’s my biggest pet peeve?
4. Do I prefer deep talks or playful banter?
5. What’s something I struggle to talk about?
6. What’s a fear I’ve shared with you?
7. What’s my love language?
8. What’s something I’m really passionate about?
9. What makes me feel most at peace?
10. What always cheers me up?
11. What’s a goal I’ve had for a long time?
12. What’s something I find really hard to forgive?
13. What’s my go-to coping mechanism when I’m stressed?
14. What’s something I daydream about?
15. How do I usually deal with conflict?
16. What kind of compliments mean the most to me?
17. What’s one value I’d never compromise on?
18. Do I consider myself more logical or emotional?
19. When do I feel most like myself?
20. What’s something I wish people understood about me?

Flirty and Romantic

Whether you’re just getting to know each other or already deep into a relationship, these questions are a fun, meaningful way to explore romantic energy. Sweet, sometimes spicy, and just vulnerable enough to build a stronger connection.

1. What do I look for in someone I like?
2. How do I act when I have a crush?
3. Do I like public displays of affection or not really?
4. What’s my idea of a perfect date?
5. Am I more of a words or actions person in relationships?
6. How do I like to be comforted?
7. What’s my favorite thing about romantic movies (even if I pretend not to like them)?
8. What physical feature do I secretly love getting compliments on?
9. Do I prefer spontaneous surprises or planned gestures?
10. What’s something small that would totally melt me?
11. Would I rather cuddle or go on an adventure?
12. How do I feel about love notes or romantic texts?
13. What song would I call “our song” if I were in love?
14. What romantic gesture do I secretly want to experience?
15. What’s my flirting style—obvious or mysterious?
16. How do I respond when someone flirts with me?
17. Do I believe in soulmates?
18. What’s one thing that makes me feel close in a relationship?
19. Do I fall fast or take my time?
20. What’s one thing I find irresistible?

This or That Challenges

Quick. Simple. Revealing. These either-or questions are deceptively easy, but they say a lot about someone’s instincts and preferences. Great for fast rounds or throwing into texts between deeper convos.

1. Coffee or tea?
2. Text or call?
3. Sweet or salty?
4. Netflix or YouTube?
5. Dog or cat?
6. Beach or mountains?
7. Day or night?
8. Winter or summer?
9. City or countryside?
10. Early bird or night owl?
11. Books or movies?
12. Organized or messy?
13. Introvert or extrovert?
14. Action or romance?
15. Hoodie or jacket?
16. Rain or snow?
17. Pizza or tacos?
18. Music or podcasts?
19. Glasses or contacts?
20. Socks or bare feet?

Dreams, Fears, and Future Plans

These questions look ahead—and within. They invite honesty about hopes, fears, goals, and the kind of life you’re building. Ideal for people you trust or want to understand on a whole new level.

1. What’s my dream job?
2. Where do I want to live someday?
3. What’s one place I absolutely want to travel to?
4. Do I want a big wedding, a small one, or none at all?
5. What’s something I hope I’ll accomplish by the time I’m 30?
6. What kind of home do I imagine myself in?
7. Do I want kids, pets, both, or neither?
8. What’s a fear I haven’t quite grown out of?
9. What’s a life lesson I learned the hard way?
10. What motivates me the most—fear or ambition?
11. What’s something that keeps me up at night?
12. Do I believe in destiny or making your own path?
13. What’s something I’m saving up for or wish I could afford?
14. What would I do if I won the lottery tomorrow?
15. What kind of legacy would I want to leave behind?
16. What’s something I want to do just once—no matter how wild?
17. If I could fast forward ten years, what would I want to see?
18. What’s something I’m scared to admit I want?
19. What do I hope people remember me for?
20. What’s one dream I’ve never told anyone?

Bonus Round: Quick Hits

This lightning-round batch is all about fast fun. Use them when things get quiet, random, or just when you want to mix it up. These questions are short but packed with personality.

1. What’s my biggest irrational fear?
2. What would I name a pet snake?
3. What show have I rewatched the most?
4. What’s a food I refuse to eat?
5. Who’s my biggest celebrity crush?
6. What’s my favorite holiday tradition?
7. What phone game do I play too much?
8. What’s the background on my lock screen?
9. What kind of weather makes me happiest?
10. If I had a catchphrase, what would it be?
11. What’s one song I never skip?
12. What’s something I always say I’ll do… but don’t?
13. What’s my favorite time of day?
14. What’s one thing I could talk about forever?
15. What’s my favorite random fact?
16. What’s the last thing I laughed really hard at?
17. If I had a secret talent, what would it be?
18. What word do I use way too much?
19. What’s my favorite guilty pleasure show?
20. What’s a habit I have that drives people crazy?