330 Questions to Ask When Online Dating

Looking to make your online dating chats more exciting and revealing? Awesome! Asking the right questions can be the key to finding a real connection.

From their favorite snack to their life goals, get ready to dive in and really get to know your match. Let’s make your conversations so much more than just “Hey, how’s it going?“

About Interests

1. What’s your favorite type of music?
2. Do you like to read? What’s the last book you read?
3. Are you into sports? Which ones?
4. What’s your go-to movie genre?
5. Do you like cooking or baking?
6. Are you a coffee or tea person?
7. What’s your favorite way to spend the weekend?
8. Do you have a favorite TV show right now?
9. Are you a morning person or a night owl?
10. Do you like to go hiking or camping?
11. What’s your favorite board game or video game?
12. Do you have any pets?
13. Do you enjoy going to concerts?
14. What’s your favorite type of food?
15. Are you into any kind of art or craft?
16. Do you have a favorite place to hang out?
17. Are you a beach person or a mountain person?
18. Do you like to dance?
19. Are you into podcasts? Which ones?
20. Do you have a favorite type of exercise?
21. What’s your favorite holiday?
22. Do you enjoy doing puzzles or brainteasers?
23. Are you a fan of any specific sports teams?
24. Do you enjoy gardening?
25. What’s your go-to comfort food?
26. Are you into fashion?
27. Do you enjoy photography?
28. What’s your favorite season of the year?
29. Do you like going to the theater or watching plays?
30. What’s your favorite type of international cuisine?
31. Are you into astrology or horoscopes?
32. Do you enjoy watching reality TV?
33. Are you into history or museums?
34. What’s your favorite kind of weather?
35. Do you like to sing, even if it’s just in the shower?
36. Do you enjoy DIY projects?
37. What’s your favorite way to relax after a long day?
38. Are you into any extreme sports like skydiving or bungee jumping?
39. Do you like watching documentaries?
40. What’s a hobby you’ve always wanted to pick up but haven’t yet?

About Personal Goals

1. What are your goals for the next year?
2. Do you want to get married someday?
3. Are you interested in having kids?
4. What’s your dream job?
5. Where do you see yourself in 5 years?
6. Do you have a “bucket list“? What’s on it?
7. What are you doing to reach your goals?
8. What’s the most important thing you want to achieve in life?
9. Are you a saver or a spender?
10. How do you feel about settling down?
11. Do you have any career goals you’re working toward?
12. What’s a skill you’d love to learn?
13. Do you believe in work-life balance?
14. How ambitious would you say you are?
15. What steps are you taking to be healthier?
16. Do you have any travel goals?
17. Is there a cause or charity that means a lot to you?
18. What’s something you want to do before you turn 40 (or 50, 60, etc.)?
19. How do you handle stress or setbacks?
20. What are you looking for in a relationship?
21. Are you interested in buying a house someday?
22. How do you define “success“?
23. What are your spiritual or religious goals?
24. Do you have a plan for retirement?
25. Is there a place you’ve always wanted to live?
26. What’s a goal you’ve recently set for yourself?
27. Do you have a five-year plan?
28. How important is it for your partner to share your goals?
29. Is there something you’ve always wanted to do but haven’t yet?
30. What would you like to be remembered for?

About Music and Movies

1. What’s the last movie you watched and loved?
2. Do you have an all-time favorite band or artist?
3. What’s a classic movie you’ve never seen but want to?
4. What type of music helps you relax?
5. Do you prefer watching movies at home or in the theater?
6. What’s the first concert you ever went to?
7. Who’s your favorite movie character?
8. What’s a song that always makes you dance?
9. Do you have a favorite movie soundtrack?
10. Who’s a musician you’d love to see live?
11. What’s your favorite movie quote?
12. Are there any musical instruments you play or want to learn?
13. What’s a movie you can watch over and over again?
14. What’s the most recent song you added to your playlist?
15. Do you like musicals? If so, which ones?
16. Do you have a favorite music genre?
17. What’s a movie that made you cry?
18. What’s a song that reminds you of your childhood?
19. Are you into foreign films?
20. Do you like going to music festivals?
21. What’s a movie that made you laugh really hard?
22. Do you have a favorite music video?
23. What’s a movie everyone loves but you don’t?
24. What’s a song you know all the words to?
25. Are there any upcoming movies you’re excited about?
26. Do you follow any music blogs or YouTube channels?
27. What’s a movie that scared you as a kid?
28. What song do you listen to when you’re feeling down?
29. Have you ever walked out of a movie? Why?
30. What’s a song that makes you feel happy no matter what?

About Travel and Adventures

1. Where’s the coolest place you’ve ever been?
2. Do you like road trips?
3. Have you ever been camping? Did you like it?
4. What’s on your travel bucket list?
5. Are you a fan of flying or do you prefer other ways to travel?
6. Do you like to travel alone or with people?
7. What’s the most adventurous thing you’ve ever done?
8. What’s a country you’re dying to visit?
9. Do you like traveling to big cities or quiet places?
10. What’s the longest trip you’ve ever been on?
11. Have you ever been on a cruise?
12. Do you like to plan out your trips or just go with the flow?
13. Are you into extreme sports like skydiving or scuba diving?
14. What’s the most beautiful beach you’ve visited?
15. Have you ever lived in another country?
16. What’s your must-have travel item?
17. Do you like to visit famous landmarks?
18. What’s the most amazing meal you’ve had while traveling?
19. Do you prefer hotels, hostels, or Airbnbs?
20. Have you ever done a spontaneous trip?
21. What’s the most challenging trip you’ve taken?
22. Do you enjoy hiking or nature walks?
23. Have you ever been to a theme park? What’s your favorite ride?
24. Do you collect anything from the places you visit?
25. What’s the most interesting cultural experience you’ve had while traveling?
26. Are you a fan of winter sports like skiing or snowboarding?
27. Do you like to take a lot of photos when you travel?
28. What’s the next place you’re planning to visit?
29. Have you ever gone on a trip for a special event, like a festival or wedding?
30. What’s the most memorable souvenir you’ve ever brought back from a trip?

About Food and Drinks

1. What’s your all-time favorite meal?
2. Do you like to cook or are you more of a takeout person?
3. Are you a fan of spicy food?
4. What’s your go-to drink when you’re out?
5. Do you have a favorite dessert?
6. Are you into wine, beer, or cocktails?
7. What’s a food you’ve never tried but want to?
8. What’s the weirdest food you’ve ever eaten?
9. Do you like breakfast foods? What’s your favorite?
10. Do you have any food allergies or dietary restrictions?
11. What’s your favorite fast-food place?
12. Are you a tea or coffee person?
13. What’s the best dish you can cook?
14. Do you prefer sweet or salty snacks?
15. What’s your favorite fruit?
16. Do you like trying international cuisines? Any favorites?
17. What’s your go-to comfort food?
18. Do you enjoy grilling and barbecues?
19. What’s your favorite ice cream flavor?
20. Do you like to bake? What’s your best recipe?
21. Are you into smoothies or juices?
22. What’s a restaurant you’ve always wanted to go to?
23. Do you like seafood?
24. What’s a dish your mom or dad makes that you love?
25. Are you a vegetarian or have you ever thought about it?
26. What’s your favorite type of bread?
27. Do you enjoy holiday-specific foods, like pumpkin spice in the fall?
28. What’s a popular food you just can’t stand?
29. Do you like to pair certain foods and drinks together, like wine and cheese?
30. What’s the most memorable meal you’ve had on a date?

About Hobbies and Free Time

1. What do you like to do on the weekends?
2. Do you have a favorite sport you like to play?
3. Do you enjoy gardening?
4. Are you into any kind of crafting, like knitting or woodworking?
5. What’s a YouTube channel you can’t get enough of?
6. Do you have a green thumb? Do you like to take care of plants?
7. Do you enjoy going to the gym or working out?
8. What’s a hobby you started during the pandemic?
9. Are you a fan of comic books or graphic novels?
10. Do you like going to flea markets or garage sales?
11. Do you have a special skill or talent, like juggling or magic tricks?
12. Do you enjoy writing or keeping a journal?
13. Do you like to fish or go hunting?
14. Are you a fan of any particular web series or online creators?
15. Do you have a favorite type of puzzle, like Sudoku or crosswords?
16. What’s an outdoor activity you love?
17. Do you like stargazing or astronomy?
18. Are you into model building or collecting anything special?
19. Do you like to paint or draw?
20. Are you a fan of escape rooms or mystery games?
21. Do you enjoy going to comedy clubs?
22. What’s something creative you’ve made recently?
23. Do you like visiting art galleries or museums?
24. Do you enjoy swimming or water sports?
25. Are you into any table games like chess or poker?
26. What’s something you do to unwind after a stressful day?
27. Do you have a favorite app or mobile game?
28. Are you interested in volunteering for any causes?
29. Do you like attending live sports events?
30. What’s a hobby or activity you’d like to get better at?

About Work and Career

1. What do you do for a living?
2. Do you like your job?
3. What’s your dream job?
4. What was your first job ever?
5. How did you get into your current line of work?
6. Do you work more with people or computers?
7. Have you ever had to move for a job?
8. What’s your favorite part about your job?
9. What’s the most challenging part of your work?
10. Are you a workaholic, or do you prefer a laid-back approach?
11. Do you like working from home?
12. Do you have to travel a lot for work?
13. What’s the most exciting project you’ve worked on?
14. Do you have any mentors or role models in your field?
15. How do you handle work stress?
16. Do you like to dress up for work, or is it casual?
17. Have you ever thought about starting your own business?
18. Do you work more for passion or for the paycheck?
19. What’s the most interesting job you think exists?
20. Are you part of any work-related organizations or groups?
21. Do you have a five-year career plan?
22. How do you keep learning and growing in your job?
23. Have you won any awards or gotten any promotions recently?
24. Do you enjoy teamwork or prefer to work alone?
25. How do you handle tough decisions at work?
26. Are you into networking events?
27. How do you feel about office politics?
28. What would make you quit a job?
29. Have you ever been your own boss?
30. What’s the most useful skill you’ve learned in your job?
31. Do you have a side hustle?
32. What’s the weirdest job you’ve ever heard of?
33. How do you feel about taking work home?
34. Do you like your boss and coworkers?
35. What’s a typical workday like for you?
36. Have you ever had to fire someone?
37. Do you have a separate work phone?
38. How do you balance work and personal life?
39. Do you have any career-related books or podcasts you love?
40. What’s a job you’d never want to do, no matter how well it pays?

About Family and Friends

1. Are you close to your family?
2. How many siblings do you have?
3. Do you have a best friend?
4. What’s your favorite family tradition?
5. Do you have any family pets?
6. Who in your family are you most like?
7. What’s the best advice a friend has ever given you?
8. Do your friends and family live nearby?
9. Who is the funniest person you know?
10. Do you have a favorite childhood memory with your family?
11. How often do you catch up with old friends?
12. Are you the oldest, youngest, or in the middle of your siblings?
13. What’s the most important quality you look for in a friend?
14. Do you have any family recipes you love?
15. What’s the most memorable trip you’ve taken with friends or family?
16. How do you handle disagreements with family?
17. Do you have any close cousins?
18. What’s the best gift you’ve ever received from a friend?
19. What’s your family’s go-to holiday destination?
20. Do you have friends from different stages of your life, like school, college, or work?
21. How do you celebrate big life events with your family?
22. Do you have a family member you turn to for advice?
23. Are there any friends you’ve known since you were a kid?
24. What’s a family event you look forward to every year?
25. Do you prefer big gatherings or small hangouts with friends?
26. Do you have family movie nights?
27. Who is your go-to person when you’re having a tough day?
28. How did you meet your closest friends?
29. What’s the best thing about your family?
30. Are there any inside jokes you share with your friends?
31. Do you have any family heirlooms?
32. How often do you talk to your closest friends?
33. What’s your family’s favorite meal to cook together?
34. Do you have any friendships that started online?
35. How important is family time to you?
36. Do you have a friend who’s like a sibling to you?
37. Have you gone on any trips with friends?
38. How do you celebrate birthdays in your family?
39. Do you and your friends have any traditions?
40. What’s the best thing a friend has ever done for you?

About Past Relationships

1. Have you been in a long-term relationship before?
2. What’s the most important lesson you’ve learned from past relationships?
3. Are you friends with any of your exes?
4. How long have you been single?
5. What’s the longest relationship you’ve been in?
6. How do you usually handle breakups?
7. What’s a deal-breaker for you in a relationship?
8. Did you ever have a “puppy love” or childhood sweetheart?
9. Do you believe in love at first sight?
10. How soon do you think is okay to say “I love you” in a relationship?
11. Are you the type to make the first move, or do you like it when others do?
12. What’s a romantic gesture that really means a lot to you?
13. Have you ever been in a long-distance relationship?
14. What’s your opinion on dating someone from the workplace?
15. Have you ever lived with a significant other?
16. How do you feel about public displays of affection?
17. Do you think opposites attract?
18. What’s a red flag for you when dating?
19. Have you ever gone through a really messy breakup?
20. Do you believe in “the one” or that there are multiple people one could be happy with?
21. Have you ever dated someone your friends didn’t like?
22. What’s your take on online dating vs. meeting people the “old-fashioned way“?
23. Have you ever had a “rebound” relationship?
24. How do you feel about discussing past relationships with your current partner?
25. Do you have any relationship regrets?
26. Have you ever taken a break in a relationship and then gotten back together?
27. Do you believe in giving second chances?
28. Have you ever been cheated on?
29. How do you feel about your partner staying friends with their ex?
30. What’s something that past relationships have lacked that you’re looking for now?

About Deal-Breakers

1. Do you have any non-negotiables in a relationship?
2. How do you feel about smoking?
3. Is political alignment important to you?
4. Do you have any deal-breakers related to kids, like wanting them or not?
5. What’s your stance on pets?
6. Is religion a deal-breaker for you?
7. How do you feel about long-distance relationships?
8. Are you okay with dating someone who’s really busy?
9. How do you feel about jealousy in a relationship?
10. Is there a certain age gap that’s a deal-breaker for you?
11. What’s your take on social media behavior, like oversharing about your relationship?
12. How do you feel about someone who doesn’t want to get married?
13. Is not wanting to move cities a deal-breaker for you?
14. How important is physical attraction to you?
15. What’s your stance on financial stability?
16. Do you have any dietary deal-breakers, like being vegan or eating meat?
17. How do you feel about someone who doesn’t like to travel?
18. What’s your take on dating someone who’s still close to their ex?
19. Is lack of ambition a deal-breaker for you?
20. Do you have a deal-breaker related to education level?
21. How important is a sense of humor to you?
22. How do you feel about someone who doesn’t exercise or take care of their health?
23. What’s your stance on open relationships?
24. How do you feel about dating someone with a lot of debt?
25. Is not being into the same hobbies or interests a deal-breaker?
26. How do you feel about someone who doesn’t read or keep up with current events?
27. Is being too introverted or too extroverted a deal-breaker for you?
28. How do you feel about someone who’s messy or disorganized?
29. Do you have any deal-breakers related to family involvement?
30. Is a lack of emotional intelligence a deal-breaker for you?

Frequently Asked Questions

When is the right time to ask more sensitive questions like those about past relationships or deal-breakers?

Timing is everything. Sensitive questions should generally be saved for when you feel a basic level of trust and comfort has been established. Usually, this is after you’ve had a few conversations and you both seem genuinely interested in each other.

What if I ask a question and the conversation stalls?

Don’t panic. If a question falls flat, it’s not the end of the world. You can always steer the conversation in a new direction with a different topic.