When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works.

The Deep Questions to Ask a Girl Every Guy Needs to Ask


A handsome face and bulging biceps are all well and good, but what a girl ultimately wants, is a guy she can connect with on a deeper level. Banter is great for flirting, but it’s those deep and meaningful conversations that really draw her in. When she feels she can talk to you about anything — and that you genuinely care about what she has to say — you have a great shot at deepening your relationship with her. And people who regularly engage in meaningful conversation by asking deep questions are far more likely to maintain an intellectually intimate connection.

Need we point out that intellectual intimacy leads to emotional and physical intimacy as well? And what guy doesn’t want that with the girl he likes?

One of the best ways to show a girl you're interested in by asking deep questions. We get it, it’s much easier said than done. That’s why we’ve come up with a list of deep, thought-provoking questions that are sure to engage any girl in conversation with you. So give them a try next time you find yourself talking to a girl you like and see how she responds.

Dating Apps That Actually Work For A Regular Guy

These deep questions work really well when talking to women online. If you aren't using at least one dating app you're missing out on tons of opportunities. So many women aren't meeting guys anywhere else. These are the best options right now to find a quality girl and practice with the questions on our list:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Great If You're Handsome
Tinder Highlights
Tinder Highlights
  • Great if you're pretty good looking
  • Very popular, especially if you're 18-22
  • Really focused on photos
  • Becoming more of a dating than hookup app
Try Tinder

The Best Deep Questions to Ask A Girl

We always recommend memorizing some of your favorite questions so that you’re prepared for every situation, be it a date or a casual chat with a girl you’re really into.

The key to success is to use the questions sparingly and at the right time to get to know someone. Never dive right into a deep topic. Make some small talk first to help warm her up for more meaningful discussion. Transition gradually into deeper topics by sharing your own thoughts or feeling first and then encourage her to do the same.

Don’t worry if a discussion stalls. That’s where this list comes in. Wait for a natural lull in the conversation and then slip in an appropriate question to get the conversation going again.

It’s also important to remember that you’re not a journalist conducting an interview. Ask a question and let the conversation flow by listening to what she has to say and then responding. You can ask a follow-up question on the same topic or recount your own experience in that particular area as well. You might be surprised by where the conversation ends up, all because of one question.

New course

A few other things to remember:

  • Make sure it’s actually a good time to talk. For instance, it should be a time when neither of you has other commitments and can focus completely on each other.
  • With that in mind, don’t try to have a deep discussion in a noisy spot like a crowded bar or a sports game. Find somewhere quiet to have relaxed and intimate conversations.
  • Choose questions that actually interest you. That way you’ll be able to stay focused on what she’s saying and will have comments of your own to add. This is a great way to get to know her.
  • Maintain eye contact while she’s talking and give cues like nodding, smiling or saying “right,” “yes,” or “really?”
  • Don’t be afraid to react to what she is saying by showing authentic amazement, surprise, confusion, sadness or whatever the situation calls for.
  • When you ask follow up questions, make them specific rather than too general. General questions will get you vague answers. If the goal is to know her better, ask her specific, pointed questions.
  • Resist any urge you have to use her story as a launchpad to talk about your own experience. Make sure she’s completely done talking about that topic before turning the conversation to you.

With all of this in mind, you’re ready to wow the girl you like with amazing questions that will not only lead to some amazing discussions but that will help you get to know one another better.

The Best Deep Questions We Know

A serious conversation between a couple

Having some deep yet interesting questions under your hat can help you in a variety of social situations from a first date to meeting a woman at a party.

Just remember, the key to making these questions truly count is to listen well to her responses and be prepared to either ask follow up questions or to share your own thoughts on the topic. When you can do that, she will know you are truly engaged and interested in what she has to say.

Here are some great deep questions to get you started:

1. If you were a man for a month, what things would you do?

This is a great question to gain insight on her opinion of you and men in general. It will also tell you a bit more about her. Is she imaginative or practical in what she decides to do?

2. What makes you feel loved or appreciated?

Not only does this show interest in her feelings, but it also gives you crucial info on how to make her feel special if your relationship progresses.

3. Do you think you have to be alone to feel lonely?

This topic can go in so many different directions from philosophical to personal. It could even lead to some shared personal experiences. Be sure to let her finish sharing before you start talking.

4. How young is too young to get married and have a family?

If you have vastly different opinions about marriage and kids it’s always better to know sooner rather than later.

5. Do you believe in free will or destiny?

This is one of those questions that could bring up personal convictions and even spiritual beliefs, so make sure you’re ready to go there if you ask this question.

H apps promo

6. If you had the choice to keep either your 30-year-old body or 30-year-old mind until you were 100, what would be your preference?

It’s pretty hard to choose between being able-bodied or having a sharp mind, but be ready with your own answer too.

7. Do life’s struggles really make you stronger?

This is one of those questions that could lead to a pretty personal discussion. So make sure you’re willing to share some of your own experiences and how it made you a better man if she asks.

8. If sleep wasn’t necessary, what would you do with all that extra time?

Can you imagine having an extra eight hours a day to get things done? Share how you’d spend that time. Try to think of some things you could do together if you had more spare time.

9. If you could control something with your TV remote, what would it be?

This question will show how good of an imagination she has. Be sure to put some thought into your answer.

10. Is it OK to lie in certain situations or should you always be honest?

Is she completely honest all the time or does she think it’s OK to tell white lies in certain situations? Or maybe she’s totally OK with lying. This is a good way to find out.

11. Why do you think truly meaningful relationships are so difficult to find?

Has she ever had a deep and meaningful relationship? You’ll likely find out once she answers this one.

12. If you could rule the world, what are the first things you would change?

This is a great way to see if you care about the same things and have the same political opinions without directly asking about politics.

13. If you were so rich that you didn’t need to work, what would you do?

Would she shop? Volunteer? Exercise more? This is a good way to find out what’s important to her.

14. If you could have the answer to one of life’s mysteries, what would you want to know?

What secret of the universe would she want to be revealed? Be prepared with a question of your own.

15. If you could have a Ph.D. and all the knowledge that goes with it, what would you choose?

Her answer might surprise you. Maybe she always secretly wanted to be a scientist or a historian.

H apps promo

16. If you found out you had one year left to live, what changes would you make to your life?

This one’s a pretty heavy topic, but it can reveal a lot about what she prioritizes in life. Would she change a little or a lot? Give some thought to your answer, too.

17. What are the top three things on your bucket list?

Knowing her biggest goals and wishes gives you valuable insight into what matters to her. Maybe you can suggest scratching some bucket list items off of your respective lists together.

18. If you had the power to abolish only one thing, would it be hunger or hatred?

What does she see as the bigger problem? Great ready for a debate if you don’t agree.

19. Your house is on fire, but no one is inside. What items would you save?

Is it her laptop, a piece of jewelry or maybe some treasured photographs? This one is another that shows insight into what she values.

20. Do you believe in fate?

Are some things just meant to be, or is it all a lot of nonsense? This question may bring out the philosopher in both of you.

21. What do you believe your purpose in life is?

This can be a hard question, especially if she’s young and still figuring things out.
If she has a good answer for this one, then she’s likely well on her way to living her best life.

22. Do you think it’s possible to forgive and forget?

Can you ever truly forget about the ways you’ve been wronged? This is a good one for a philosophical debate.

23. If you could travel to the past, would you change your life in any way?

Back to the Future may warn against changing the past, but would she take the chance to make her life better?

24. Name three things that always make you happy.

Knowing what makes her happy can help you to make her happy too because you’ll know what’s essential to her.

25. If you could talk to anyone for one hour, who would it be?

Would it be someone she’s lost, a family member or someone famous? There are so many options.

26. Who is the most interesting person you’ve ever met?

Discovering who captivates her should give you an idea of how well she’ll fit into your life and vice versa.

27. Is homelessness a problem in our country? Should people try to help them?

Not only will this tell you if she has compassion for others, if she has a well-thought-out answer, but you’ll also know she genuinely cares about social issues.

29. Do you like trying new things? Have you tried anything new lately?

How adventurous is she? Let’s hope her level of spontaneity matches yours! You can even make a pact to try something new together every month.

30. What’s more your style: a day at the beach or a campfire under the stars?

They both sound like fun. Why not suggest doing whatever one she picks together for a first (or next) date.

Promotion for best dating apps article

31. Do you believe God exists?

Shared faith can be a powerful thing. It’s always good to believe in the same things if you’re hoping for a serious relationship.

32. Is it important to go to church?

If she does believe in God, this is a good one to ask to find out if she’s serious about her faith.

34. Have you ever had a life-changing experience?

Not everyone has had such a defining moment, but those who have always have a great story to tell.

35. Have you ever had a brush with death?

This may or may not be something she wants to talk about. Don’t push her if she’s experienced this but doesn’t want to share the details.

36. Do experiences shape you as a person or do you think people shape their experiences?

Does she consider herself to be the mistress of her own fate? Or does she think something bigger is at play?

37. Is true wealth a state of mind or is it just about the size of your bank account?

This question should reveal what her priorities are and how important — or unimportant — she considers wealth.

38. Is it ever hard for you to accept defeat?

Is she stubborn or does she give up easily? Is she a good match for you in this area?

39. What are the most important social issues today?

It’s always good to know what the girl you like cares about and to see if you share similar opinions on current issues.

40. Do you follow politics? Do you try to stay informed?

Can she tell you all about her elected officials or is she uninterested in government? This question definitely gives you a good chance to see how well informed she is

41. Is it important for people to vote during elections?

Does she take her civic duty seriously or is she completely uninterested in politics?

42. Do you think it’s possible to find true love more than once in a lifetime?

Is she a romantic, a realist or a mixture of the two? This will tell you.

43. Should a couple live together first or wait until marriage?

What are her views on cohabitation? This question will tell you what she expects should your relationship progress to that level.

44. Are you shy, outgoing or somewhere in between?

Are you the same or is this a case of opposites attracting?

45. Do you consider marriage to be the ultimate goal in a relationship?

It’s always good to know what she’s hoping will come out or romantic relationships — that way you can make sure you both ultimately want the same thing.

Course promo

46. Have you ever said “I love you” first in a relationship?

Does she fall in love easily or is she more guarded?

47. When is the last time that you laughed so hard you cried and why?

Knowing what makes her laugh will help you to understand her better.

48. What do you consider more essential to a relationship: physical intimacy or emotional intimacy?

Both are important, of course, but what can’t she do without?

49. Do you hope to get married and have children one day?

This is vital to know, especially if you have strong opinions on both subjects.

50. What’s the most important lesson a parent can teach a child?

Knowing what she’d want her child to learn will also tell you what values she thinks are most important in herself and others.

Dating Apps That Actually Work For A Regular Guy

These deep questions work really well when talking to women online. If you aren't using at least one dating app you're missing out on tons of opportunities. So many women aren't meeting guys anywhere else. These are the best options right now to find a quality girl and practice with the questions on our list:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Great If You're Handsome
Tinder Highlights
Tinder Highlights
  • Great if you're pretty good looking
  • Very popular, especially if you're 18-22
  • Really focused on photos
  • Becoming more of a dating than hookup app
Try Tinder

Deep Questions to Ask Your Crush

A man talking to his crush at a cafe

Asking questions that are deep and personal shows your crush that you’re truly interested in getting to know her. These questions vary from deep and intensely personal, to light and fun, so make sure you choose questions that accurately reflect how well you know each other.

51. Do you like to plan or be spontaneous when you travel?

Is she a serial planner or a fly-by-the-seat of her pants kind of gal? It’s probably best if you agree on this one or you might drive each other crazy on a vacation.

52. Is waiting for marriage romantic or unrealistic?

Does she think sex is only for marriage, for a committed relationship with her boyfriend or something to be enjoyed with anyone she’s attracted to?

53. Do you think Hollywood sets unrealistic expectations for love and relationships?

Is she influenced by what she sees on the silver screen or does she go her own way?

54. What one personality trait of yours would you want your children to have?

This should tell you what she likes the most about herself.

55. What one physical trait of yours would you want your children to have?

This is another one that will reveal what she likes about herself, but this time physically.

56. If your children were the same way you were as a teenager, would you be worried or pleased?

Was she a hellion or a little angel? Would you have been compatible in high school?

57. If you could have three things to make you happy, what would you choose?

This question is the perfect way to find out what she values most.

58. What was your favorite cartoon when you were a kid? Do you still like it?

Everyone has a favorite. If you like the same cartoons, why not have a cartoon marathon?

59. Would you rather have a baby without a partner or a partner without a baby?

Does she value a relationship more with an equal partner or would she rather be a parent?

60. Is it important to give people second chances?

How forgiving is she? This could be pretty important to know if you’re hoping for a relationship with her.

Course promo 2

61. Have you ever been “mansplained” and, if so, what did you do about it?

How does she handle herself in tough situations? Is she aggressive, passive or does she know how to assert herself while still being polite?

62. Who was your first crush?

Everyone has a first love. And they always make for at least a few good stories.

63. Do you think people fall in love because they’ve met the right person or because they’re at the right time in their life, regardless of who the person is?

Does she believe in soulmates or that multiple people could be “the one?”

64. What do you look for in a romantic partner?

Knowing this is key to your success. Hopefully you match up well with what she’s looking for!

65. Are you willing to ask a guy out, or do you prefer to be asked?

Is she the type of girl who enjoys making the first move or does she like being pursued. Either way, take your cue from her answer.

66. Have you learned any important lessons from past relationships?

Sharing experiences from past loves — and how they’ve shaped you — can bring you closer together.

67. Are you more of a morning person or are you a night person?

If she’s a night owl, you’ll know a late-night movie marathon is sure to make her smile. If she’s a morning person, an early walk followed by breakfast at her favorite restaurant is a great suggestion to make.

68. What’s your favorite way to exercise?

Is she a hard-core fitness buff, a couch potato or something in between?

69. What do you think is your best physical attribute?

This is a good question for discerning how confident she is. If she has a healthy amount of confidence, she should have no problem answering this one.

70. If you had to choose three adjectives to describe yourself, what would they be?

How does she see herself — and is she honest about who she is? This should let you know.

71. Did you ever wish you had superpowers when you were a kid? Which ones did you wish for?

72. Where would you rather spend your time, swimming at the beach or hiking?

73. What mythical animal speaks to you the most?

74. Which family member are you closest to and why?

75. If you could live anywhere without cost being a factor, where would you choose to live?

76. What quality in a person makes you fall in love with them?

77. Has anyone ever broken your heart?

78. If you had to pick a song as your personal soundtrack, what song would you choose?

79. What was your favorite subject in school?

80. Do you sing in the shower? If so, what are your go-to songs?

Deep Conversation Starters

Asking questions that are conversation starters

Sometimes you need the perfect sweet thing to say or question to spark a conversation. The best conversation starters not only show your interest in her but are questions that require more than a "yes" or "no" answer. If you want to get the girl you like talking, asking her these deep questions that will get her thinking are one of the best ways to do that. Here are some of our personal favorites:

81. What three words would you choose to describe yourself?

Don’t forget to ask follow-up questions about each of the words they chose. If she said she’s organized, for instance, ask her what she does to stay that way.

82. What’s your idea of a perfect weekend?

Finding out what they like and value always gives you plenty to talk about, especially if you share some of the same interests.

83. What is the most controversial opinion you have?

Don’t ask this one unless you are prepared for a good-natured debate if you disagree on something. If you can’t agree to disagree, you may want to steer clear of this one!

84. Has anything in the news captured your attention lately?

Knowing what she’s interested in beyond her own life is always a good thing.

85. If you could discover one thing about your future, what would you want to know?

Would she ask something specific or would she simply want to know if she was going to live a long, happy life?

Does she love Instagram and hate camo print clothing?

87. What are the things you most hope to accomplish before old age?

What are her goals in life? Do you have any similarities?

88. Have you ever done any volunteering?

This is a great way to find out what she’s passionate about — and how maybe you can serve together.

89. What inspires you the most?

Is it a book, music or maybe some advice she was given? Finding out what motivates her is a great way to get to know each other better.

90. What is mankind’s greatest invention in your opinion?

Is she impressed with technology, medicine, fashion advances — there’s so much to choose from.

New course

91. Do you think humans will ever be replaced by machines in most aspects of life?

Is she worried about a future where AI will take over?

92. Have you seen any movies lately that really made an impression on you?

What kind of movie or story really moves her or ignites her imagination? Find out and suggest watching it together.

93. Have you read any good books lately?

If she’s a reader, ask if she can recommend something for you to read. Then make sure you read it so you can discuss it together. (Hint: Only ask this question if you actually enjoy reading too).

94. Have you ever been married?

This is a good one to know. If she’s been married, she could be carrying baggage from a marriage that didn’t work out or she could be grieving a loss. It’s best to make sure neither is fresh if you’re hoping for a relationship with her.

95. Are humans doing more harm than good to the earth?

It’s always good to know what she thinks about environmental issues.

96. Do you think psychics are real or are they scammers?

Is she a believer or a skeptic?

97. Would you rather be perceived as vain or insecure?

While neither is ideal, how she answers will reveal a lot about how secure she is.

98. Would you rather be a rule follower or a rule breaker?

Does she believe in following her conscience? Is she a rule breaker for the heck of it? Or does she prefer to follow the letter of the law?

99. What is your idea of the perfect vacation?

This is good to file away for the future. Maybe you can take her on her dream vacation one day.

100. Do you have any unusual hobbies?

As long as it’s not a totally off-the-wall pastime, you can ask her to be your instructor. It’s practically a guaranteed date!

101. Do you consider yourself an introvert, an extrovert or a combination of the two?

102. Are you friends with your co-workers, or do you keep your personal and professional life separate?

103. If “hello” and “hi” had to be replaced by another greeting, what would that greeting be?

104. Does your family have any unusual traditions that you absolutely love?

105. What would your perfect life look like?

106. What quote or saying inspires you?

107. Do you believe in soulmates or is that just wishful thinking?

108. What was the first movie you ever watched in the theatre?

109. Have you ever slept outdoors? Did you enjoy it?

110. Would you rather watch a sunrise or a sunset?

Deep Questions to Ask Your Girlfriend

Asking his girlfriend questions

The better you know your girlfriend, the better your relationship and the closer you’ll be as a couple. Here are some great deep questions that will not only help you get to know your girlfriend better, but will help you build a more powerful emotional and physical connection with her.

111. What was the first thing you thought about this morning?

What’s on her mind? You? Work? The weather? Sometimes, sharing even random thoughts like these can increase emotional intimacy between you.

112. What would you change about our relationship if you could?

Don’t ask this one unless you’re actually willing to accommodate her wish!

113. What’s your favorite memory of us as a couple?

Knowing what memories she cherishes most will help you to ensure you have many more similar ones in the future.

114. What was your first impression of me when we met?

If you didn’t make a good first impression, don’t be offended. She’s with you now so you obviously made a good second impression!

115. If you could make three wishes — and I had to fulfill them — what would they be?

Absolutely do not ask her this unless you’re ready to make her wishes come true!

H apps promo

116. What’s your definition of husband material?

This question is best asked only if you’re serious about each other. It will definitely help you to understand what she expects if you do get married.

117. What’s your guiltiest pleasure?

Her guiltiest pleasure could be anything from a favorite treat to a music group she’s embarrassed to admit she likes. If you want her to think of more intimate things, just do a little gentle prodding.

118. Is there such a thing as love at first sight?

Has she ever fallen hard for a guy? This will tell you if she’s more impetuous or careful.

119. Are there any romantic gestures that you’d like to have in our relationship?

Again, don’t ask this question if you’re not interested in being more romantic. Otherwise, she’ll be left very disappointed.

120. Where do you most like to be kissed?

Once you know her magical spot, make sure you give it a lot of attention.

121. What do you find a major turn on?

It’s always good to know what your girlfriend likes both in and out of bed.

122. What is your biggest turn-off?

The same goes for what she doesn’t like!

123. What would be your perfect night for us as a couple?

Knowing her ideal scenario will give you some great ideas for how you can surprise her sometime with her perfect outing.

124. Do music and lighting help get you in the mood?

Making her completely comfortable is key to a great time together!

125. How long should a couple date before discussing marriage?

It’s always a good idea to know what her expectations are.

126. What things are most likely to cause a marriage to fail?

This question will tell you what you might be most likely to fight about if you get married — unless you both agree on the subject, of course.

127. What’s your idea of a perfect wedding?

Being well-matched on wedding expectations is a good thing, so hopefully you have the same ideas.

128. What would be your perfect honeymoon?

This is a good one to discuss if you are planning to get married. Planning ahead could help you to score a deal on your dream trip as man and wife.

129. Have you thought about what kind of wedding ring you’d want?

Knowing what her ring style is will help you pick out an engagement ring she loves.

130. Do you think finances are important in a marriage?

If she says no, you’ll know she’s either naive or truly doesn’t care about financial security.

131. Would you want to get counseling if you felt like your marriage was in trouble?

132. What are the top three things that every healthy marriage needs?

133. Would having kids make your bond as a married couple stronger or does it put a strain on your relationship.

134. Do you like children?

135. Do you want to have children someday and if so, how many?

136. How do you think work, child-rearing and household chores should be divvied up?

137. What qualities would you want the father of your children to have?

138. Would you want to go back to work, give up your job to raise the kids or work from home?

139. Would you cook dinner every night, want me to cook or share the responsibility?

140. What do you think of renewing wedding vows? Is it something you’d ever want to do?

Top hookup apps that experts recommend

With so many flaky users, it’s no wonder the online hookup game is getting harder and harder to win. But with these tried and tested hookup apps and sites that give REAL RESULTS, finding someone who’s up for anything can be a breeze!

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Great If You're Handsome
Tinder Highlights
Tinder Highlights
  • Great if you're pretty good looking
  • Very popular, especially if you're 18-22
  • Really focused on photos
  • Becoming more of a dating than hookup app
Try Tinder

Deep Questions to Ask a Girl over Text

Replying to texts while smiling

If you find it hard to think of clever conversation when texting with the girl you like, worry not. Whether you want to make her think about you in a whole new way or just get a conversation going, these deep questions can help. Not only will they give you some better insight into her personality and character, but you’ll also be able to come off as interesting and fun to talk to.

Here are some of the best questions to learn more about a girl via text.

141. If you could read minds, whose would you read?

Would she want to read your mind or is there someone else’s thoughts she’s dying to know?

142. What do you think our generation will look back on and laugh?

Terrible Tinder dates? Cringy TikTok trends? Questionable fashion choices? Whatever she chooses, it should spark an interesting conversation.

143. Where have you traveled and what’s your favorite travel memory?

Knowing where she’s gone and what she’s done is not only an interesting topic to discuss, it also tells you more about her and her interests.

144. If you were lost on an island and you could take five people with you for company, who would they be?

There’s no better way to learn who means the most to her.

145. Have you ever met someone that you felt like you knew from a previous life?

If she says yes, you’ll know she’s not your average, conventional person.

146. What do you think you’ll be most nostalgic about 50 years from now?

Will she be nostalgic for a simpler time like childhood? Or maybe for time spent with her kids? It’s hard to choose.

147. If you could travel anywhere simply by snapping your fingers, what would be your destination of choice?

Would she pick somewhere relaxing, exciting, interesting? The sky’s the limit.

148. Is there one thing that you believe everyone should try at least once before they die?

Is it something she has done herself or simply wants to try?

149. Is there anything that you secretly like that you’re too embarrassed to tell people about?

Everyone loves something that they’re just a little bit embarrassed about. Be sure to share your secret too. Fair is fair.

150. If you could travel through time, would you go to the past or the future?

Is she a history buff or does she long to see the future’s innovations?

151. Would you choose a tropical vacation for two or a long weekend camping together?

Is she satisfied with simple pleasures or does she long for the finer things in life?

152. What do you think of blind dates? Have you ever been on any?

If you’ve both been on blind dates, there are always some fun stories to be told.

153. Have you ever gone out with a guy you met online?

This is another question that can lead to some interesting stories about the experiences you’ve both had.

154. How do you handle stress?

Knowing how she handles stress can clue you in on what to do when she’s stressed out.

155. How long should a couple date before living together?

This will tell you her expectations for your future relationship.

156. If you had to put them in order from most to least important, how would you prioritize money, love and career satisfaction?

Hopefully your answers line up!

157. Do you have a happy place that always makes you feel good?

Where does she go to relax, de-stress and feel comforted? Make sure you share your own safe haven with her.

158. What pastimes make you feel relaxed and happy?

Does she have hobbies that help her de-stress? Suggest trying them together.

159. Do you have any personal goals you’re working toward?

What’s important to her? There’s no better way to find out.

160. How important is physical attraction in a relationship?

Does she need to have immediate chemistry with a guy to pursue a relationship?

161. Do you like animals? Do you have a pet?

162. Do you have a large family?

163. Are you a sensitive person?

164. What’s your idea of a great workout?

165. What do you think of astrology?

166. Do you find it hard to admit when you’re wrong?

167. What are the top three books you’ve ever read?

168. What song never fails to put you in a good mood?

169. What three apps do you use the most on your phone?

170. Would you rather call or text?

Deep Flirty Questions to Ask a Girl

A flirty couple engaged in a conversation

It’s always good to be prepared with some good questions to ask the girl you’re talking to, whether you’re on a date or are simply engaging in some banter at a party.

No matter how smooth of a communicator you are, you should be prepared with some interesting questions for when the conversation stalls. Having a few deep flirty questions memorized can help you avoid awkward silences. It might also help you build some attraction!

Here are some flirty questions sure to spark her interest in you:

171. Do you need to like someone to be physically attracted to them?

Has she ever had a spark with a guy she didn’t even like? Hopefully you’ll like each other and share an attraction.

172. What’s the first thing you notice about a man?

Is she more into the physical or does she place more weight on personality?

173. Kissing on the first date. Yea or nay?

Knowing this before your first date will help you to decide whether to go for it or not.

174. Have you ever dated more than one guy at a time?

Is she a one-man woman or does she like to play the field?

175. Where are the top three places you’d like to go on a date?

Again, this gives you valuable information if you do start dating, so be sure to pay attention to her answer.

176. If money and distance weren't factors, where would you want to go on a date?

It’s good to know — in case you ever win the lottery.

177. Have you ever tried online dating? If so, was it a good experience?

If you’ve both used dating apps you can swap your best stories.

178. Have you ever found a woman attractive sexually?

Has she ever been with, or thought about being with a woman?

179. Is it important to be friends with your lover?

Does she want a man she can like and trust or is she just looking for passion?

180. What’s the most romantic thing a man can do for you?

Make sure you remember her answer and, if you end up in a relationship, you can surprise her with a grand gesture.

H apps promo

181. Do you like to cuddle?

Make sure you’re ready to cuddle up with her if she says yes!

182. What is your opinion on casual sex? Is it OK or something you don’t approve of?

If it’s not something she’s into, make sure you respect that even if it’s something you’re OK with.

183. Is there anything you'd do only with your husband, but not with a boyfriend?

Does she consider anything sacred to a marriage? Be sure you respect her wishes.

184. Are you still a virgin? If not, when did you lose your virginity?

Remember it’s tit for tat, so be ready to share the story of your first time too.

185. What regret in love has made you wish you could turn back time?

Does she have any regrets from her past? Do you? Shared reget can be a good bonding experience.

186. What do you look for in a romantic partner?

Learning her criteria and priorities is a good thing if you’re hoping to be — or stay — in a relationship with her.

187. What do you find attractive about me?

This is a good way to find out if she is indeed attracted to you. Once you find out what she likes, be sure to play that feature up as best you can.

188. Have you ever tried role-playing? If not, is it something you’d ever consider doing?

You might not want to ask this one unless you’ve actually been intimate.

189. Would you ever relocate for love?

Would she follow you if you got a job in a different state?

190. Do you still remember your first kiss?

Did she have a good or forgettable first experience? Swap first kiss stories to see who has the best one.

191. Is physical intimacy necessary to have a good relationship?

192. What is the most loving thing you have ever done for someone?

193. Name one bad quality that you actually wouldn’t mind in your partner.

194. How many pillows do you sleep with at night?

195. Have you ever been moved to tears during sex?

196. Do you know what your love language is?

197. What’s better? A scalp massage or a foot rub?

198. Would you rather have a candlelit dinner in a fancy restaurant or a picnic under the stars?

199. Do you and your friends talk about your sexual experiences or is that something you keep private?

200. Would you rather receive flowers or sexy lingerie from your boyfriend as a gift?

Deep Personal Questions to Ask a Girl

A deep and serious conversation

Thought-provoking, personal questions are a great way to get to know the girl you like better. Just make sure you’re ready to share some personal information too. She’ll expect you to share just as much as she does.

Here are some of the best deep personal questions to ask:

201. What’s the best advice you’ve ever received?

This might not be one she’ll be able to answer immediately, but there’s always a few people in our lives who’ve given us good advice.

202. Is there anything you take for granted that you should be thankful for?

It can be hard to remember to value something we’ve always had. What does she value the most?

203. Is spirituality important to you?

This is another question that touches on personal beliefs. Does she believe in God or another entity? If your spiritual beliefs are important to you, this is a question you should ask.

204. Who is the one person you look up to more than anyone else?

Whether it’s her grandmother or someone famous, this question will reveal what’s important to her.

205. Have any aspects of your life improved in the past 5 years?

Is she an optimistic person, a realist or a pessimist? This question will let you know.

Promotion for best dating apps article

206. What’s a deal-breaker for you in a romantic relationship?

If you’re hoping to have a relationship with her, this is a good one to know because it will help you to change your behavior or find out that you’re not compatible.

207. How would you like people to remember you?

Her answer should reveal a lot about what she values most in life.

208. If you were to open a business right now, what would it be?

This is where you’ll get to learn more about her passions and interests. Be sure to think through what you would do if she asks you the same.

209. What is your best character trait? Your worst?

Not only does this question tell you how well she knows herself, but also how honest she’s willing to be with you.

210. Does the past matter when it comes to relationships?

Whether you agree or not, make sure her answer is one you can live with.

211. If you could enjoy any view out of your window, what would it be?

If she’s more of a realist, she might respond with her favorite type of scenery. If she's less conventional she may offer up a more unusual answer.

212. What do you think a lot of people are missing out on simply because they don’t know about it?

Whether it’s an unusual food, a little known place or an unconventional type of music, offer to give it a try with her as your instructor.

213. Have you ever been left speechless because of a personal experience?

This question can lead to a lot of sharing, so be sure to have a moment of your own to talk about.

214. Have you ever made a mistake that helped you to learn and grow as a person?

Everyone makes mistakes, so what has she learned from hers?

215. What’s the best gift you’ve ever bought for someone?

Is she thoughtful or creative in her gift-giving? Maybe she’s more of a gift card person. Either way, it will give you an idea of what you can expect in the future.

216. How many relationships have you had?

Knowing how many relationships she’s had should give you a good idea of whether she’s into long-term commitment or not.

217. If the guy you were in love with proposed after one year of dating, how would you react?

Does she think one year is enough time? It’s good to know for the future.

218. What book has influenced you the most?

Learning what book means a lot to her is a good way to get to know her, especially if you’ve read the book too.

219. How do you feel about infidelity? Is it ever OK? Is it forgivable?

It’s always good to know her take on this — a couple needs to be on the same page.

220. Have you ever done anything embarrassing for a friend?

This can lead to some pretty interesting or even funny stories. Be ready to share some of your own.

221. Is there anyone in your life who you’d protect, even if it meant dying?

222. Have you ever made someone cry?

223. Have you ever made a decision that you felt guilty about afterward?

224. What do you think of the #MeToo movement?

225. If you were to die tonight, would you die satisfied or unsatisfied with your life?

226. If you could be born in another time period, what era would you choose and why?

227. Which would you choose for transportation: a bike, a horse, or a car?

228. What would be better: to win the lottery or work at your ideal job?

229. What accomplishment are you most proud of?

230. What always motivates you to do your best?

Course promo

Deep Questions to Ask a Friend

Friends chatting at a cafe

If you’re friends with lots of girls, you’re a lucky guy. They are great for practicing your conversational skills on — so why not try these questions out on them? Not only will you get to know them better as friends, but you’ll see how valuable deep questions are in engaging a girl’s interest.

231. If you received a package containing $1 million, what would you do with it?

How would she spend her unexpected windfall? This one will give you insight on her values and what’s most important to her.

232. If the world was coming to an end tomorrow, would you want to know?

Would she rather try to prepare herself for the end or to live her final day blissfully unaware?

233. Is fearing the unknown understandable or a simple waste of time and energy?

This question will show if she’s practical, imaginative or a mixture of the two.

234. Are there any social customs that you hate and would like to see disappear?

While this question can really make you think, it’s also pretty funny as you discuss the merits of air-kissing someone’s cheek or if you think shaking hands is ridiculous.

235. What’s the first thing you think of when you hear “less is more?”

Is it perfume? Salt? This is a great question to see if she’s more practical or more creative.

236. What always makes you laugh?

Whether it’s a funny movie, memory or a friend, do your best to share this favorite thing with her.

237. What’s the worst thing a person can do without actually breaking the law?

This question is another one that will lend insight to her morals. Whether she says lying, gossiping or something else altogether, be sure you never exhibit any of that behavior.

238. What’s the most ridiculous thing you’ve ever done because you were bored?

Boredom can be the ideal breeding ground for creativity. Share your best stories on how you both alleviated your boredom.

239. How would you celebrate a major personal victory like getting a new job or surpassing a major fitness goal?

What’s her idea of a celebration? If you know what she likes, you can surprise her when a big event occurs.

240. What topic could you give a 20-minute presentation on without preparing ahead of time?

Everyone’s an expert on something. What does she know a lot about? Let her educate you.

241. Is there anything you would change about yourself if you could?

This is a good way to learn about each other's insecurities and vulnerabilities. Be sure to share your own.

242. If you had to eat the same meal every day for the rest of your life, what would you choose?

It’s always good to know what your bestie’s fave meal is.

243. If you had the money to hire someone would you want them to clean your house, cook your meals or do your yard work?

All three would be nice, which one would you pick?

244. What is your all-time favorite movie and why?

Discussions about movies are always great. Watching favorite movies together is even better.

245. Did you eat something regularly as a child that you now can’t stand?

Did your pal eat so many peas as a kid that she’s now completely traumatized by them? Be sure to tease her accordingly.

246. What’s your record for going without sleep (and why did you)?

Can you beat her record? Swap stories to see who’s the victor.

247. If you could go on a vacation for free to either Alaska or Mexico, which would you choose?

A free vacation is always welcome, but would she choose warm weather or cool forests?

248. If you had to star in a reality TV show, which one would you choose?

Would she make up one of her own, or would she rule the ratings on a current show?

Course promo 2

249. What in life gives you the most joy?

It’s always good to know what brings happiness to your friends.

250. Are there any skills or traits you wish you had?

What does she wish she could do? Be sure to point out to her all the things she does rock at.

251. Do you believe in the supernatural? Is it scary or interesting to you?

252. If you had to choose one religion to be devout in, which would pick and why?

253. What is your motto for day-to-day life?

254. If you were handed a cheque for $5,000 and were told to spend it however you wished, how would you use it?

255. Which of these values do you consider the most important: Honesty, kindness or courage?

256. What is your definition of beauty?

257. Do you believe in deja vu?

258. Tell me your best “and then it got worse” experience.

259. Have you ever made an innocent mistake that had major consequences?

260. What do you think the best part of old age will be?

Dating Apps That Actually Work For A Regular Guy

These deep questions work really well when talking to women online. If you aren't using at least one dating app you're missing out on tons of opportunities. So many women aren't meeting guys anywhere else. These are the best options right now to find a quality girl and practice with the questions on our list:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Great If You're Handsome
Tinder Highlights
Tinder Highlights
  • Great if you're pretty good looking
  • Very popular, especially if you're 18-22
  • Really focused on photos
  • Becoming more of a dating than hookup app
Try Tinder

Deep Would You Rather Questions

A couple having a funny conversation

If you’re ever at a loss for words, a rousing game of "would you rather" can get the conversation rolling again. This new game is already a classic because it never fails to get people thinking — and laughing — and, ultimately having a lot of fun. Playing this game allows you to ask pretty deep questions, but they're also super fun!

261. Would you rather never pay taxes again or have four months of paid holidays every year?

Both options are pretty attractive. Learning why she’d choose one over the other can give you some pretty good insight into the way she thinks.

262. Would you rather know about everything and or have everything surprise you?

This can lead to a discussion on some of the best or worst surprises you’ve had or even ask her ways she’d like to be surprised.

263. Would you rather forgive or get even?

Once again, this one has the potential to get deep with a discussion about morals and beliefs, or you can make her laugh with crazy schemes to get even with the person who cut you off in traffic.

264. Would you rather give bad advice or take bad advice?

This can get philosophical about the importance of putting others’ needs first or you can keep it light — and keep her laughing — by coming up with some of the crazy advice you’d give.

265. Would you rather have one wish granted right now or wait five years and have three wishes granted?

This is a great conversation starter because you can talk about all the things you’d wish for if you could from being able to eat as much as you wanted without gaining weight to being able to magically avoid traffic. You can keep it light or you can go deeper with more personal desires.

266. Would you rather have the ability to control time or to fly?

Once she gives her answer, you can talk about what you’d do with your abilities. You’d be able to spend more time with her or be able to fly to her side whenever she needs you. Both answers are sure to win you brownie points.

New course

267. Would you rather publish your most personal thoughts or have a movie made about your most embarrassing moment?

This is a good chance to get her laughing by telling her your most embarrassing moment or by coming up with something zany to publish, like that crazy dream you had the other night. This will also get you sharing personal moments and thoughts, and nothing builds a bond between two people more quickly than that.

268. Would you rather have a desk job or work with your hands?

Both types of work have their merits. Which one would she prefer?

269. Would you rather marry your true love or win millions in the lottery?

Is she all about love or does she love money more?

260. Would you rather live in a beautiful cabin in the woods or a hut on a tropical island?

Knowing her choice will help you choose a good destination for a getaway together.

261. Would you rather have lots of casual friends or one close friend?

Is she more about popularity or true friendships?

272. What would you rather do in the evening, watch television, play a game, visit a relative or read?

Is she a social butterfly or does she cherish some quiet alone time?

273. Which household chore would you rather always do: wash and dry the dishes, cut the grass, clean the bathroom or vacuum the house? Which chore would you rather never do?

This is good to know — especially if you ever live together. You can take on the job she hates the most.

274. Would you rather talk in rhyme or sing everything you say?

Both would be funny — for maybe half an hour.

275. Would you rather wear a ball gown or a bikini everywhere you go?

Be sure to tell her she’d look gorgeous in either option.

276. Would you rather lose the ability to read or the ability to speak?

This is a hard one. Which does she value more?

277. Would you rather give up dessert or alcohol for life?

Could she truly give up chocolate forever in favor of wine?

278. Would you rather go for one month without Wi-Fi or one month without bathing?

Hygiene or connectivity. What’s it gonna be?

279. Would you rather be super strong or super fast?

The possibilities are endless for both. If you both choose different powers, you’d be the ultimate team.

280. Would you rather only be able to whisper or only be able to shout?

Both would get pretty annoying after a while.

281. Would you rather have all traffic lights turn green whenever you drive or never have to stand in line again?

282. Would you rather have the ability to control time or to fly?

283. Would you rather eat the same meal for the rest of your life or give up social media?

284. Would you rather go about your daily routine completely naked or take a year-long nap?

285. Would you rather find your true love or a suitcase with $5 million inside?

286. Would you rather be alone for the rest of your life or be surrounded by annoying people for the rest of your days?

287. Would you rather be held in high regard by your parents or your friends?

288. Would you rather always be 10 minutes late or always be 20 minutes early?

289. Would you rather go to prison for a year or lose one year off of your life?

290. Would you rather marry a super hot jerk or an ugly man who is kind, smart and funny?

H apps promo

Funny Deep Questions

Asking "would you rather" questions

If you want to make a girl laugh without resorting to silly antics or coarse humor, these funny questions that are also deep are perfect. Not only will they help you get to know her better, but they’ll keep her engaged in an enjoyable and interesting conversation with you.

291. Would you rather be a super-rich or super smart or a supermodel?

Her answer to this will tell you what she values most.

292. If you could give yourself a nickname, what would you want people to call you?

Try to come up with a flattering nickname that you’d give her. It’s a good way to offer her a compliment without being too obvious.

293. Is it more fun being a kid or being an adult?

There are pros and cons to both, of course, but getting her take on it can lead to a pretty interesting discussion.

294. Is the glass half-full or half-empty?

Is she an optimist or a pessimist?

295. If you could be a fly on the wall, what situation or conversation would you eavesdrop on?

Would she want to know what people really think of her or would she be hoping to pick up some insider political info? Or maybe she’d use her ability to advance her career or help someone in need.

296. If you could win an Olympic medal for everyday activities, what activity would you win gold in?

Whether it’s something silly like painting her toenails in record time or being able to recite the Pledge of Allegiance backward, be sure you have a suitable crazy talent of your own to share.

297. Would you rather be served a home-cooked breakfast in bed every day for a week or have a maid clean your entire house?

Either option would be amazing. And, if she chooses breakfast in bed, you can offer to prepare her a few!

298. If you could become fluent in a new language at the snap of a finger, which language would you choose?

This question will make her think, but it’s also fun and can lead to a discussion about other countries and future vacations. Be sure to have an answer of your own as well.

299. If you had to either go bungee jumping or skydiving, which would you choose to do?

Which, for her, is the lesser of two evils? Or maybe she’s a daredevil and would do both!

H apps promo

300. Do you like guys who ask a lot of questions?

If she says yes, feel free to ask as many questions as you want from this list as long as you don’t do it like you’re interrogating her! If she says no, it could be that she’s a private person and you’ll have to be careful not to overdo it.

301. Which fictional character most closely resembles your personality?

Does she have a TV doppelganger or does she identify with someone from literature?

302. If you were told you had to turn into a zombie or to die, what would you choose?

Let’s face it, both choices suck. Which one is worse for her? What about for you?

303. If you were an action figure toy, what accessories would come with you?

Give this one some serious thought so you can impress her with your add-ons.

304. Have you ever pulled a great practical joke? What was it?

Was she the mastermind of a great prank? Make sure you compliment her cunning.

305. Would you ever trust a boyfriend to buy an outfit for you?

If she says yes to this one, you may need to up your shopping game.

306. Is there anything you like that is traditionally considered a “guy thing?”

Maybe you’ll luck out and she’ll share your hobbies.

307. If you were handed a cheque for $20,000 and were told you could only use it to upgrade your shower or bathtub, which would you choose? What upgrades would you make?

That would be a pretty amazing shower or bathtub!

308. What would you do if everyone you had ever known had vanished from earth?

How would she survive without any support system? What would you do? Share your thoughts.

309. If you were going to dedicate your life to solving one single problem, what would it be?

This question is a good way to learn more about what’s important to her.

310. What is the strangest wrong number text or phone you’ve ever received?

This one can make for some pretty funny stories. Tell her your own too.

311. Have you ever wished you could swipe left and swipe right on people in real life? What would happen to them if you could do that?

312. If the color blue had a taste, what would it taste like?

313. Have you ever felt real hatred toward a fictional villain?

314. When does your brain go on autopilot?

315. Are there any silly things that you take a lot of pride in?

316. If you could choose anyone to be the next president of the United States, who would it be?

317. If you had to participate in a dance competition, what song would you dance to?

318. If you were going to star in a reality TV show, what would it be?

319. What would be the worst thing ever to put into a piñata?

320. If you were to become rich, what wild and crazy things would you do?


Join Our Newsletter

No Spam. Just Higher Dating Success.

Leave a Comment