220 Questions to Ask When Online Dating

Online dating can feel like a wild mix of excitement and awkwardness, can’t it? Swiping, matching, and chatting with someone new is fun, but figuring out what to ask them? That’s a whole different story.

You want to seem interesting (without trying too hard), get to know them (without sounding nosy), and keep the conversation flowing (without a million awkward silences).

The truth is, knowing what to ask can make all the difference. Whether you’re looking for a laugh, gauging their relationship goals, or trying to spot those sneaky red flags, asking the right questions can turn a bland chat into something meaningful—or save you from wasting time on someone who’s clearly not your match.

Questions to Ask a New Match

1. What made you decide to try online dating?
2. How would your friends describe you in three words?
3. What’s your favorite way to spend a weekend?
4. Are you more of an early bird or a night owl?
5. What’s one fun fact about you that surprises people?
6. Do you prefer coffee, tea, or something else entirely?
7. If you could live anywhere in the world, where would it be?
8. What’s the last book you read or show you watched?
9. Do you enjoy traveling, or are you more of a homebody?
10. What’s your go-to comfort food?
11. Are you into pets? If so, dogs, cats, or something else?
12. What’s the most adventurous thing you’ve ever done?
13. Do you enjoy meeting new people or prefer smaller circles?
14. What’s your favorite type of music or band?
15. What’s something you’ve always wanted to try but haven’t yet?
16. Are you into fitness or any specific sport?
17. What’s your ideal vacation: relaxing on a beach or exploring a city?
18. Do you enjoy cooking or prefer dining out?
19. What’s one thing that always makes you laugh?
20. What’s something simple that brings you joy?

Funny Questions to Ask on a Dating App

1. What’s the weirdest thing you’ve ever eaten?
2. If you could have a useless superpower, what would it be?
3. What’s the most embarrassing thing that’s happened to you in public?
4. Would you rather fight one horse-sized duck or 100 duck-sized horses?
5. What’s your guilty pleasure TV show or movie?
6. If you could only eat one food for the rest of your life, what would it be?
7. Do you have a pun or dad joke that never fails?
8. What’s the strangest talent you have?
9. If animals could talk, which one would be the rudest?
10. Would you rather always sing instead of talking or always dance instead of walking?
11. What’s the funniest text you’ve ever sent by mistake?
12. Have you ever tried something just because it looked cool on social media?
13. If you could swap lives with a cartoon character, who would it be?
14. What’s your favorite absurd conspiracy theory?
15. If your life were a movie, what genre would it be?
16. What’s the silliest thing you’ve ever been competitive about?
17. If you could turn any inanimate object into a pet, what would it be?
18. What’s your go-to karaoke song (even if you can’t sing)?
19. Do you have a nickname that you secretly love or hate?
20. What’s a childhood habit you’ve never quite grown out of?

Thoughtful Questions to Ask on a Dating App

1. What’s one thing you’re really passionate about?
2. If you could relive one day from your past, which would it be?
3. What’s a life lesson you’ve learned recently?
4. What’s something you value most in a friendship or relationship?
5. If you could master any skill instantly, what would it be?
6. How do you typically handle challenges or setbacks?
7. What’s the best piece of advice you’ve ever received?
8. Is there a quote or saying that inspires you?
9. What’s one thing you’d like to achieve in the next five years?
10. How do you like to spend your downtime?
11. What’s one cause or issue you deeply care about?
12. Who has had the biggest influence on your life?
13. Do you prefer planned-out days or spontaneous adventures?
14. What’s something you’ve been wanting to learn more about?
15. How do you usually celebrate your achievements?
16. If money weren’t a concern, how would you spend your time?
17. What’s one thing people often misunderstand about you?
18. What’s your definition of happiness?
19. If you could travel in time, would you go to the past or the future?
20. What motivates you to get out of bed in the morning?

Values and Beliefs

1. What values do you prioritize most in your life?
2. How do you typically express gratitude?
3. Is religion or spirituality important to you?
4. How do you define success?
5. Do you believe in fate, free will, or a mix of both?
6. What’s your approach to giving back to your community?
7. How do you handle ethical dilemmas?
8. Are you more traditional or progressive in your beliefs?
9. Do you believe people can truly change?
10. How do you like to celebrate holidays or traditions?
11. What’s your perspective on forgiveness?
12. How do you approach helping others in need?
13. Do you see yourself as more optimistic or realistic?
14. What’s one belief you used to hold but no longer do?
15. How important is honesty in a relationship for you?
16. Do you prefer stability or are you open to taking risks?
17. How do you feel about personal growth and self-reflection?
18. How do you usually make tough decisions?
19. Do you think people should follow their heart or their head?
20. How do you define a fulfilling life?

Interests and Hobbies

1. What’s a hobby you could never give up?
2. How do you like to spend a lazy Sunday?
3. Are you more into outdoor activities or indoor hobbies?
4. What’s a new hobby you’ve picked up recently?
5. Do you enjoy reading, and if so, what’s your favorite genre?
6. What’s the most unusual hobby you’ve ever tried?
7. Are you into video games or board games?
8. Do you prefer solo hobbies or ones you can do with others?
9. What’s the last concert or live event you attended?
10. Are you more into sports or arts and crafts?
11. What’s a skill or craft you’ve always wanted to learn?
12. Do you enjoy cooking, baking, or experimenting in the kitchen?
13. What’s your favorite way to stay active or fit?
14. Do you enjoy exploring new places in your free time?
15. Are you into collecting anything?
16. What’s your favorite type of movie or TV show?
17. Do you enjoy photography or taking creative photos?
18. What’s your favorite way to unwind after a long day?
19. If you had unlimited time, what hobby would you pursue?
20. Are you more into creating things or experiencing them?

Evaluating Lifestyle Compatibility

1. Are you more of a city person or a countryside person?
2. What’s your ideal work-life balance?
3. How do you typically spend your weekends?
4. Do you prefer a fast-paced life or a more laid-back lifestyle?
5. Are you an organized person or do you prefer going with the flow?
6. How do you feel about traveling often?
7. Do you enjoy hosting people at home or prefer keeping things quiet?
8. What’s your approach to fitness and health?
9. How do you feel about sharing responsibilities in a household?
10. Do you enjoy socializing frequently or prefer smaller gatherings?
11. Are you more spontaneous or a meticulous planner?
12. What’s your morning routine like?
13. Do you prefer eating out, ordering in, or cooking at home?
14. How do you manage your downtime?
15. What’s your approach to budgeting or financial planning?
16. Are you comfortable with pets in the house?
17. Do you like decorating and personalizing your living space?
18. How do you feel about work-from-home versus office jobs?
19. Do you believe in having “me time,” and how much do you need?
20. How do you usually recharge when you feel stressed?

Personal Growth and Self-Improvement

1. What’s one habit you’re currently trying to improve?
2. How do you usually set and track your goals?
3. Do you enjoy reading or listening to self-help content?
4. How do you handle constructive criticism?
5. What’s a recent challenge you overcame, and how did you do it?
6. Are you into journaling or reflecting on your day?
7. What’s one area of your life you’d like to improve?
8. How do you stay motivated during difficult times?
9. Do you believe in continuous learning, and what’s a skill you’ve worked on?
10. How do you celebrate your personal achievements?
11. What’s your favorite way to stay productive?
12. How do you balance your personal and professional goals?
13. What’s one thing you’re currently proud of about yourself?
14. How do you approach big life transitions or changes?
15. What’s a quality you admire in others that you try to embody?
16. Do you practice mindfulness or meditation?
17. How do you like to push yourself out of your comfort zone?
18. What’s one thing that inspires you daily?
19. How do you typically recover from setbacks?
20. Do you have a personal mantra or guiding principle?

Deepening Emotional Connection

1. What’s one memory that always makes you smile?
2. What’s your love language, and how do you express it?
3. How do you usually handle conflicts in relationships?
4. What’s something you’ve never told anyone but feel comfortable sharing now?
5. How do you define emotional intimacy?
6. What’s one thing you look for in a close relationship?
7. How do you feel about vulnerability in relationships?
8. What’s a moment in your life that shaped who you are today?
9. How do you usually express gratitude?
10. What’s one thing you wish more people understood about you?
11. What makes you feel the most appreciated in a relationship?
12. How do you handle feelings of sadness or disappointment?
13. Do you believe in unconditional love?
14. How do you usually comfort someone you care about?
15. What’s one thing you value most in deep connections?
16. How do you celebrate meaningful milestones in relationships?
17. What’s your biggest fear when it comes to relationships?
18. What’s your happiest childhood memory?
19. How do you like to show support for someone you love?
20. What’s your idea of a perfect day with someone special?

Red Flags and Deal Breakers

1. How do you handle conflicts or arguments?
2. Have you ever ghosted someone or been ghosted?
3. How do you feel about jealousy in relationships?
4. Are you open to discussing financial habits?
5. Do you consider yourself dependable or flaky?
6. What’s your approach to maintaining friendships while dating?
7. How do you usually react when plans don’t go your way?
8. Have you ever struggled with commitment?
9. What’s your stance on honesty, even if it’s uncomfortable?
10. How do you handle accountability when you’re wrong?
11. What’s your view on balancing independence and partnership?
12. How do you feel about discussing ex-partners?
13. Are you generally punctual or late?
14. What’s one behavior you can’t tolerate in a partner?
15. Do you prefer frequent communication or less contact?
16. How do you feel about sharing responsibilities in a relationship?
17. Are you open to feedback about your actions or decisions?
18. How do you typically react to stress or frustration?
19. Do you believe in giving second chances?
20. How do you handle setting and respecting boundaries?

Exploring Relationship Intentions

1. Are you looking for something casual or a serious relationship?
2. How do you define a successful relationship?
3. Are you open to marriage or long-term commitment in the future?
4. What’s your timeline for major relationship milestones?
5. Do you see children in your future?
6. How do you feel about maintaining individuality in a relationship?
7. What’s your idea of a healthy partnership?
8. How do you typically show affection in relationships?
9. Are you comfortable talking about finances in a relationship?
10. What’s your stance on long-distance relationships?
11. How do you feel about traditional versus modern relationship roles?
12. Do you believe relationships should be 50/50?
13. How do you usually resolve disagreements with a partner?
14. What’s one quality you admire in a potential partner?
15. How do you feel about blending families or social circles?
16. Are you open to compromise on major decisions?
17. What’s your opinion on public displays of affection?
18. How do you see yourself supporting a partner emotionally?
19. Do you believe love can grow over time, or should it be instant?
20. What’s your vision for an ideal relationship?

Dating and Past Relationships

1. What did you learn from your last relationship?
2. How do you typically handle breakups?
3. What’s your opinion on staying friends with an ex?
4. Have you ever been in a long-distance relationship?
5. How do you usually express love in a relationship?
6. What’s the longest relationship you’ve ever been in?
7. Do you believe in second chances in relationships?
8. How do you usually recover after a breakup?
9. What’s one thing you want to do differently in your next relationship?
10. Have you ever been cheated on or cheated? How did you handle it?
11. How do you feel about discussing past relationships with a new partner?
12. What’s your biggest takeaway from your dating history?
13. How do you feel about dating apps versus meeting in person?
14. What’s the best date you’ve ever been on?
15. Have you ever been in love, and how did you know?
16. How do you feel about traditional dating versus modern trends?
17. What’s one red flag you ignored in a past relationship?
18. How do you usually handle arguments or disagreements?
19. What’s one quality in a partner you used to overlook but now value?
20. How do you balance independence and togetherness in a relationship?

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Frequently Asked Questions

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Final Thoughts

Don’t overthink it. Keep it light when it feels right, dig deeper when the moment calls for it, and always trust your gut.

Remember, online dating is as much about discovering yourself as it is about finding someone else. The more honest and curious you are, the closer you’ll get to finding the connection you’re looking for.

After all, dating is meant to be exciting—not stressful. So, relax, enjoy the process, and don’t forget to have a little fun along the way!