150 Questions to Ask Your Girlfriend to Deepen Your Connection

Whether you and your honey are in those super-romantic, early days of dating, or you've been together a lot longer, one of the best ways to take your relationship to the next level is simply by talking. But sometimes sharing your deepest desires, innermost thoughts and most profound memories isn't easy. How do you even get that kind of conversation started? We suggest taking a gander at the following questions to ask your girlfriend you'll find below. We've come up with 150 thought-provoking queries that are sure to open up the lines of communication between you both, leading to the kind of meaningful discussions that can only strengthen your bond.

Looking for deep or serious questions to ask her over a long, lingering dinner in, or maybe during a leisurely weekend wander? No worries, we've got you covered, along with a selection of flirty, funny and more random suggestions perfect for inspiring a less intense chat. From questions about her philosophy on life to the worst date she's ever been on and what gives her butterflies, these will all help you learn more about the woman who just might be (or definitely is!) the one. You can even try combining one of the questions with words of affirmation and maybe even a sweet gift, and then sit back and watch her eyes light up!

1. What are your thoughts on life after death?
2. How do you think your parents have influenced your view of romantic relationships?
3. What does success look like to you?
4. How do you cope with stress or sadness?
5. What's the greatest obstacle you've had to overcome?
6. When is it ever okay to lie, if it ever is?
7. What's the best advice anyone ever gave you?
8. What was the worst decision you ever made?
9. When were you happiest?
10. What scares you more than anything else?
11. Who or what inspires you?
12. Do you believe in free will or fate?
13. If you had one thing to do over, what would it be?
14. What’s the most important lesson you’ve learned about yourself?
15. Would you sacrifice your life for someone else's?
16. What character quality have you lost along the way that you wish you still had?
17. What gives your life meaning?
18. How do you experience spirituality, if you do?
19. How would you describe your philosophy on life?
20. What do you think is the greatest challenge facing humankind?
21. What would you give up to pursue your dreams?
22. What makes you really angry?
23. What life experience changed you the most?
24. Would you rather people think of you as kind, smart or attractive?
25. Do you think people can change?
26. What is something that makes you feel awe?
27. How would you like to be remembered?
28. Do you believe in giving people second chances?
29. What are your core values?
30. What makes you jealous?

1. What isn't an Olympic sport but should be?
2. Do you talk to pets in a baby voice?
3. What's your guiltiest pleasure?
4. If you had a personal assistant, what would you ask them to do?
5. Who are your weirdest friends?
6. What Jeopardy category would you crush?
7. What villain do you secretly admire?
8. If you could jump in a time machine, what historical period would you visit?
9. Do you laugh when you're alone?
10. Who would play you in a movie about your life?
11. If you came with a warning label, what would it say?
12. What's your go-to karaoke song?
13. What's your most embarrassing story?
14. What's your walk-up song?
15. What's the weirdest food you like?
16. Which celebrity would make you totally starstruck if you met them?
17. What's your six-word memoir?
18. Do you sleep with a fan on all year?
19. What's your most-hated trendy phrase or term?
20. How would we do if we were stranded on a desert island together?
21. Would you rather be able to fly or breathe underwater?
22. What's the strangest fact about you I don't know?
23. What celebrity couple do we remind you of?
24. How would you do in a zombie apocalypse?
25. Who's the last person you would want to be stuck in an elevator with?
26. If you had to smell one scent forever, which one would you pick?
27. What story does your family tell about you to tease you?
28. What is one thing you'll never do again?
29. What’s the worst date you've been on?
30. Could you land a plane if the pilots passed out and you had to?

1. Do you believe in twin flames?
2. What's your favorite love song?
3. When did you decide you wanted to be with me?
4. What's your love language?
5. What does falling in love feel like to you?
6. What's your ideal date night?
7. Do you think love can last a lifetime?
8. Have you ever used a pick-up line and if so what was it?
9. Did you fantasize about a dream wedding when you were a little girl?
10. What makes you feel sexy?
11. How do you feel about PDA?
12. What is your best memory of us?
13. What is your favorite flower?
14. How do you like to celebrate Valentine’s Day?
15. What gives you butterflies?
16. Are there any hobbies you'd like for us to try together?
17. What's your vision for our future?
18. What makes our relationship work so well?
19. Do you believe in love at first sight?
20. What's you're favorite make-out music?
21. Have you ever gone skinny dipping?
22. What feels romantic to you?
23. Do you remember what I wore on our first date?
24. How do you like to be kissed?
25. What's your perfect Sunday morning?
26. Do you ever go commando?
27. Do you believe love really can conquer all?
28. Who was your first crush and was it requited?
29. When was the last time someone made you blush?
30. What's one of your turn-ons?

1. Why did your last relationship end?
2. What's a goal you're working toward?
3. How do you like to be comforted?
4. If you could start a non-profit, what would it benefit?
5. Have you ever cried in public?
6. What qualities are important to you in an S.O.?
7. Was your childhood happy?
8. What makes you feel safe?
9. What do you judge yourself most harshly about?
10. Is there anything you wish you could change about me?
11. What are the signs I should look for when you're feeling down?
12. What do I do that triggers you?
13. How would you characterize yourself politically?
14. What are the most important characteristics of a healthy relationship?
15. What is your dream job?
16. How do you define commitment in a relationship?
17. How do you balance your work and personal life?
18. How do you engage in self-care?
19. What's your favorite creative activity?
20. What are your financial goals and do you have a plan to reach them?
21. Are you a risk-taker?
22. How do you deal with failure?
23. What are your best qualities?
24. What was the worst thing that ever happened to you?
25. What three things are you most thankful for?
26. Where do you see yourself in five years?
27. Have you ever broken someone's heart?
28. Do you like being alone?
29. What do you think we need to work on in our relationship?
30. What's the worst injury or illness you've ever had?

1. What's a question you've wanted to ask me but haven't?
2. What should everyone know more about?
3. What do you like to do when it's rainy?
4. What book changed your life?
5. What's the best compliment you've ever gotten?
6. Have you ever sought (and gotten) petty revenge on someone?
7. Do you like sad movies?
8. If you won $100,000 in the lottery, what would you do with it?
9. How did people treat you in high school?
10. Who is your favorite artist?
11. What's the most adventurous thing you've ever done?
12. Who is the one person, past or present, you wish you could meet?
13. Where is your favorite place in the world?
14. Do you consider yourself competitive?
15. Do you prefer the mountains or the sea?
16. Have you ever joined a protest?
17. What fictional character is most like you?
18. What is a secret you've never told anyone?
19. Are you more of an early bird or a night owl?
20. What's the worst job you ever had?
21. What skill would you like to learn?
22. What social norm would you get rid of if you could?
23. Have you ever lied about your age?
24. If your house was on fire what item would you save first?
25. What's your favorite season?
26. What's the number one item on your bucket list?
27. Where would you love to visit if you could travel anywhere?
28. What's your favorite way to get exercise?
29. What was your favorite TV show as a kid?
30. What's a controversial theory that you believe in?

Jill Gleeson

Jill Gleeson is a travel journalist and memoirist based in the Appalachian Mountains of western Pennsylvania who has written for websites and publications including Good Housekeeping, Woman’s Day, Country Living, Washingtonian, Gothamist, Canadian Traveller, and EDGE Media Network. Jill is the travel editor for Enchanted Living. Learn more about her journey at gleesonreboots.com.