164 Uncommon First Date Questions – Easily spark conversations

Every man who is dating needs good first date questions.

…Because there’s no avoiding it; first dates are nerve-racking. Thinking of questions to ask becomes harder when a cute girl is sitting across from you.

But it doesn’t have to be as long as you have some questions to ask on a first date memorized.

In previous posts we’ve told you how to get a girlfriend and shared some ridiculously helpful first date tips.

In this post we bring you our favorite first date questions guaranteed to keep the conversation flowing smoothly. All you have to do is remember them on your date!

Contents

19 Best First Date Questions

Start the date off strong with these 19 best first date questions. They’re great for spurring an interesting conversation, which is what you want.

Here are 19 of the best first date questions: 

1. What do you like to do in your free time?

Know her hobbies. Maybe you can join her in one.

2. Who is the most fascinating person you’ve met?

She might have an interesting story to tell.

3. What was the last book you really got into?

If you don’t read, you definitely should. I recommend Cloud Atlas for seasoned readers and The Golden Compass for newbies.

4. What are some movies you really enjoyed?

This might give you an idea of the types of movies she enjoys.

5. What amazing adventures have you been on?

If there’s a second date, plan an amazing adventure for the two of you.

6. What are you kind of obsessed with these days?

Do you ever go through a phase where you can’t get enough of something? She does too!

7. What TV series do you keep coming back to and re-watching?

It’s something to bond over.

8. What hobbies would you like to get into if you had the time and money?

Some hobbies are far too expensive.

9. Among your friends, what are you best known for?

Friends are friends because they refuse to forget something embarrassing you did once.

10. What music artist do you never get tired of?

I have one.

11. What are some obscure things that you are or were really into?

There’s lots of little niches out there for us to enjoy.

12. What are some things everyone should try at least once?

What experience left a lasting impression on her?

13. What are you always game for?

Now you have something to do immediately.

14. Where’s the strangest place you’ve ever been?

What’s her definition of “strange”?

15. Where would your friends or family be most surprised to find you?

Where does she generally avoid?

16. What do you like but are kind of embarrassed to admit?

We all have our guilty pleasures.

17. If you could go back in time as an observer, no one could see you, and you couldn’t interact with anything, when would you want to go back to?

Time travel is a sticky subject but it’s fascinating.

18. What’s been the most significant plot twist in your own life?

She didn’t see it coming.

19. How much social interaction is too much for you?

Is she an introvert or extrovert at heart?

20 First Date Conversation Starters

If you can’t seem to figure out a topic, try out these first date conversation starters.

Conversation starters do exactly what they sound like: Get a conversation started. They’re also a ton of fun to ask.

Here are 20 first date conversation starters:

20. What pets have you had?

I hear that after 8 failed relationships women get a free cat! One step closer to crazy cat lady status.

21. What’s your favorite international food?

There is too much delicious food out there to be a picky eater.

22. How many siblings do you have?

This is a great way to discuss what growing up was like for her.

23. Who is your favorite author?

This is why reading is important. So you can answer this question.

24. What was the last show you binge-watched?

Sometimes you can never get enough of a show.

25. If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?

This one is funny and will definitely make her laugh, which is always a plus.

26. What’s your favorite app on your phone?

You can check this by seeing which app has used the most battery lately. It’s in your settings somewhere.

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

Most hikers on the Appalachian Trail give each other trail names.

28. What country do you never want to visit?

There is lots of strife in the world. Who has it worst these days?

29. What is the most beautiful view you’ve seen?

What sight will she never forget?

30. What did you do last summer?

Music festival? Trip to the beach?

31. What did you do for (last holiday)? Or What will you do for (next closest holiday)?

Get to know a little bit more about how she celebrates holidays.

32. Best and worst flavor ice cream?

Careful with this question as it can spur an argument.

33. What TV shows did you watch when you were a kid?

Those shows will be rebooted in 10 years.

34. If you opened a business, what type of business would you start?

Many people have dreams to start their own business. What’s her dream?

35. What’s your favorite thing to do outdoors? How about indoors?

This is a sneaky way to get second date ideas.

36. What’s the most spontaneous thing you’ve done?

Spontaneity is the spice of life and forges lasting memories of any given moment. Be more spontaneous.

37. What’s your go-to funny story?

Always have a few funny stories of your own to throw into a conversation.

38. What’s your favorite quote or saying?

Words often inspire us to think about things a little differently.

39. If you unexpectedly won $10,000, what would you spend it on?

A quick bout of fun and excitement or a lasting investment?

22 Get To Know You Questions To Ask on A First Date

When you want to get to know someone, you ask them get to know you questions!

Get to know you questions are a little more personal (which are perfect questions to ask a girl you like.) Because lets face it… You want to get to know her.

What better way than with questions to ask a girl to get to know her?

Here are 22 get to know you questions to ask on a first date:

40. Are you a morning person or a night owl?

Not everybody wants to get the worm.

41. What’s your favorite restaurant?

Take her there on a future date!

42. What would be your dream job?

What would she do if she didn’t have to worry about money.

43. What would your perfect vacation look like?

Remember the answers to questions like these. If things go well, you’ll have things to do together and she’ll be impressed you remembered.

44. What would your perfect morning be like?

How can you start her day off right?

45. Who are your kind of people?

We all have a type of people we prefer to be with.

46. What odd talent do you have?

Can she do some strange nonsense with her tongue or joints?

47. What would you like to know more about, but haven’t had the time to look into it?

You have a pocket computer so why not look into it together right now?

48. Have you ever joined any meetup groups?

Or has she ever been apart of a group of people doing something positive in her community?

49. What’s the most relaxing situation you could imagine?

Never underestimate a day spa. Those places are Heaven on Earth.

50. Where was your favorite place to go when you were a kid?

Many of us have a favorite place from our childhood. Maybe she’ll take you there one day.

51. If you found a briefcase filled with 1 million in 100$ bills in front of your door, what would you do with it?

I would work towards making more money.

52. What’s the worst advice someone has given you?

Who lost her trust with one simple recommendation?

53. Besides your home and your work, where do you spend most of your time?

Where does she spend most of her free time?

54. What do you care least about?

We never really think about the things we don’t care about.

55. What are people often surprised to learn about you?

Sometimes we do things people don’t expect us to.

56. What would you do with the extra time if you never had to sleep?

Humans could accomplish so much if we didn’t have to sleep.

57. When you were a kid, what seemed like the best thing about being a grown up?

You can stay up as late as you want! You can eat whatever you want! But your body will hate you for it.

58. If you could send one letter to yourself in the past without the goal of making yourself rich (no lotto numbers, stock picks, etc.), what age would you choose and what would the letter say?

Unrelated note: Is anyone interested in a rare Beanie Baby collection?

59. How different do you act when you are with acquaintances vs. people you are comfortable with?

Is she more reserved in the beginning but wild and crazy as time goes on?

60. What’s your go-to series or movie when you want to watch something but can’t find anything to watch?

Netflix should have a “surprise me” button.

61. What do you like to eat to cheer yourself up?

Does ice cream really cheer someone up?

17 First Date Never Have I Ever questions for couples

One of the great weapons in your first date arsenal are your never have I ever questions. These questions always spark a great conversation. Of course, not every one of these questions work on a date, that’s why you want never have I ever questions for couples, which are focused on making that tete-a-tete a little more tender and fun.

Here are 17 first date never have I ever questions for couples:

62. Never have I ever fallen asleep on my partner while watching t.v.

One of the great joys of coupledom that you can imagine together.

63. Never have I ever dreamed of my wedding with my partner.

Basically, never have I ever been in a truly serious relationship.

64. Never have I ever been on a double date.

A fun alternative to explore if the first date is a success.

65. Never have I ever sang at karaoke.

Veteran or newbie, this is a great way to transition to the karaoke bar for more fun.

66. Never have I ever had a date just to hurt another person.

It’s cruel, but sharing that story will establish a lot of intimacy.

67. Never have I ever found someone of the same gender attractive.

Find out just how fluid their sexuality is.

68. Never have I ever helped a stranger on the street.

Are they demonstrably kind-hearted or do they just walk past the miseries of life like the rest of us?

69. Never have I ever tried to get the password of another person.

How much do they snoop around on friends and potential romantic partners?

70. Never have I ever taken something from a hotel room.

What kind of weirdo doesn’t take the free shampoo?

71. Never have I ever kissed on the first date.

Good to know before the date is over.

72. Never have I ever been on a dating website.

How old-school is their dating experience?

73. Never have I ever dated more than one person at once.

Find out now if there’s more competition to worry about after the first date’s a hit.

74. Never have I ever dated someone for more than a year.

Does she do commitment? You know the answer now.

75. Never have I ever spied on an ex online.

She either has or she’s a liar.

76. Never have I ever made fun of someone.

Whether it’s an innocent tease, a childish prank, or serious bullying she regrets, there’s a story there.

77. Never have I ever watched keeping up with the Kardashians.

If not, she’s a keeper.

78. Never have I ever lied to a friend to avoid a greater evil.

How pure at heart or practical is she?

16 Funny First Date Questions To Ask

Everyone loves to laugh. And everyone likes being around people who make them laugh.

So if you want people to like you more, you should probably have some funny questions to ask on hand. As for the ladies…

If you’re still working on asking her out, take a look at our funny questions to ask a girl. They’re written especially to get her interested in you.

Here are 16 funny first date questions to ask:

79. What fad did you never really understand?

The older you get, the harder it is to understand fads.

80. What’s the silliest fear you have?

What spooks her that shouldn’t?

81. If you lived to 100, would you rather keep the body or the mind of yourself at 30 until you were 100?

A good looking body or a healthy mind?

82. What’s the strangest phone conversation you’ve ever had?

Ever have a weirdo call and drone on about nonsense?

83. What machine or appliance in your house aggravates you the most?

Some technology never works when we want it to.

84. What’s the worst movie you’ve ever seen?

There are plenty to choose from.

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

Boredom breeds creativity. Some of humanity’s greatest achievements have come from boredom.

86. What’s happening now, that in 20 years people will look back on and laugh about?

If we laugh depends on if we make it to 20 years.

87. If the company you work for / the college you go to had an honest slogan, what would it be?

You can do this with any corporation or business. It’s a very fun game.

88. Which is the cheesiest pick up line someone has used on you?

Use your cheesiest pick up line after asking this question for either a giggle or a stern look of disapproval.

89. What is your weirdest “quirk”?

We all have them. They make us unique.

90. If you ruled the world, what would your change?

How would you create the perfect utopia?

91. What is something you have tried, but will never do again?

Sometimes breaking out of our comfort zones makes us realize we never want to try that again.

92. What’s the weirdest thing you’ve ever eaten and liked?

And sometimes breaking out of our comfort zones makes us realize we do want to try that again.

93. If you could be a man for just one day, what would you do?

A classic fun one sure to produce some laughs.

94. What is the most embarrassing thing that happened to you in school?

That one moment your entire social status in high school was up for debate.

29 Random First Date Questions

Being a little odd and quirky is one of those things that has mixed results with people.

Some people like random questions while other people aren’t too keen on them. Regardless of how anyone feels about how strange and random you can be, you should keep being yourself (unless you’re overbearing.)

So if you’re feeling a little goofy and the mood is right, random questions to ask a girl can be your best friend!

Here are 29 random first date questions:

95. Cutest animal? Ugliest animal?

Pugs are somehow cute and disgusting at the same time.

96. What’s your favorite piece of furniture you’ve ever owned?

Every piece of furniture has a story, especially in college.

97. What household chore is just the worst?

Some chores are more enjoyable than others!

98. How techie are you?

Because I’ve been having this problem with my laptop…

99. What’s expensive but totally worth it?

What items are worth a high price tag?

100. Before you make a call, do you rehearse what you are going to say?

It’s always smart to be prepared.

101. When was the last time you sang to yourself or to someone else?

We all sing to ourselves from time to time!

102. When was the last time you walked for more than an hour?

It’s important to stay active, especially as you grow older.

103. What would make for an excellent new ice cream flavor?

Strawberry toothpaste and chives.

104. What’s the most interesting fact you know?

It’s always smart to have a few random facts to throw out there.

105. What’s your favorite smell?

Don’t underestimate a good (or bad) smell. They stick with you.

106. What’s the most amount of people you had to present something in front of?

Presenting something to a class or an auditorium are both equally nerve-racking.

107. What’s the strangest way you’ve become friends with someone?

Has she met a new friend in an odd way? What’s the story?

108. What sports would be funniest if the athletes had to be drunk while playing?

Every sport is fun to play while drunk, but which would be funniest to watch?

109. What’s your favorite band NAME (not necessarily your favorite band)?

The name doesn’t always match the sound.

110. How well do you cope when you don’t have your phone with you for an extended period of time?

Those little distraction devices are hard to live without.

111. If you had the power to change one law, what law would you change?

What would she like to get away with?

112. How would you feel if you were in a white room with people all dressed in white?

How did you get there in the first place?

113. If you had power to transform into a bird, what type of bird and which bird would you want to become?

Zip through the forest as a Wren or soar across the sea like an Albatross?

114. If you were in a forest, what are the three emotions you’d feel?

Is she a nature lover?

115. Do you squeeze the toothpaste from the middle or the end?

I’ve seen both tactics ruin friendships between roommates.

116. Have you ever felt like you met someone in a previous life?

Maybe reincarnation really does exist. What are the implications if it does?

117. If you could read minds, how would you use the gift?

Would she destroy her opponents or make the world a more bearable place?

18 Would You Rather Questions to Ask On A First Date

Would you rather questions are always fun to ask, no matter the situation.

So I highly recommend you ask some of the following for a successful first date.

Here are 18 would you rather questions to ask on a first date:

118. Would you rather live full time in an RV or full time on a sailboat?

Ocean life or land lubbing?

119. Would you rather have an incredibly fast car or incredibly fast internet speed?

Zoom zoom.

120. Would you rather have true love or win the lottery?

Money can’t buy happiness, but it can buy cake.

121. Would you rather marry a nice guy or a flirty one?

Flirty doesn’t always mean dishonest and nice doesn’t always mean faithful.

122. Would you rather spend 2 months living in a nursing home or spend a 2 weeks eating only from Taco Bell?

“It’s time for lunch Gertrude. Today we ordered Taco Bell for you and the other residents!”

123. Would you rather go to an amusement park or a family reunion?

Lots of thrills or lots of family?

124. Would you rather work behind a desk or with your hands?

Being stuck doing one you don’t like is emotionally draining.

125. Would you rather be a hard worker or a smart worker?

Work smarter, not harder.

126. Would you rather live in a cabin in Alaska or on a tropical island?

Both will be the first to go when the earth heats up.

127. Would you rather have no sense of smell, or have a sense so strong you could smell everything around you like it was in front of your face?

Before you decide, read up on why your sense of smell is so important!

128. Would you rather go for a bungee jump or hot air balloon ride?

Thrilled or chilled?

129. Would you rather live for 6 months in a light house, accessible only by a 3 mile boat ride, or live for 6 months in the most crowded room of a youth hostel?

All the personal space you can imagine or no personal space at all?

130. Would you rather be able to stop time at will or age at half the normal human rate?

You have a leg up in society with either power.

131. Would you rather be confined to your home for one month and only able to communicate with the outside world via fax machine or unable to go back to your home for 3 months?

Home is where the fax is.

132. Would you rather have many causal friends or one close one?

Someone you know you can count on or a bunch of someones you might be able to count on?

133. Would you rather have a mansion or a cozy home that has just the right amount of room?

Tiny houses have become more and more popular over the years.

134. Would you rather have an exotic meal in a five-star hotel or a delicious chocolate-cake from a local bakery?

Fancy feast or tasty treats?

135. Would you rather be someone else’s first love or their last forever?

Either is a lot of pressure.

19 Deep First Date Questions To Ask

Deep questions to ask are fantastic questions for when the conversation gets a little more personal.

They deal with our deepest thoughts and feelings, which you’ll want to know when talking to a girl you like. We have other deep questions to ask a girl, but below are some hand-selected ones specifically for a first date.

Here are 19 deep first date questions to ask:

136. What would you do if had enough money to not need a job?

What would she do if all of her time was free time?

137. What are some accomplishments that you are really proud of?

She should be proud of herself if she’s ever going to be proud of you.

138. If you could give everyone just one piece of advice, what would it be?

What if they followed it?

139. Do you prefer to work in a team or alone?

Is she a team player or a loner?

140. How have you changed from when you were in high school?

You never think you’ll change but you do.

141. When do you feel most out of place?

Being uncomfortable helps us grow into stronger versions of ourselves.

142. What says the most about a person?

My personal answer is how they treat animals.

143. If you could have the answer to any one question, what question would you want the answer to?

There are so many unanswered questions. Choose wisely.

144. What do you miss about life 10 or 20 years ago?

Nostalgia is a powerful drug.

145. What’s getting worse and worse as you get older? What’s getting better and better as you get older?

With age comes new struggles and things to be thankful for.

146. What’s the best way to get to know who someone really is?

How can you truly understand a person?

147. Who besides your parents taught you the most about life?

Our parents don’t teach us everything.

148. If you could instantly receive a Ph.D. in any discipline including all the knowledge and experience that goes along with it, what would your Ph.D. be in?

What would she enjoy being an expert in?

149. What friendship you’ve had has impacted you the most?

Sometimes we lose track of friends but we never lose track of how they made us feel.

150. What’s the hardest you’ve worked for something?

Dedication and discipline are attractive. You should practice them.

151. How much personal space do you need to be comfortable?

Personal bubbles range in size all over the world.

152. If you knew you were going to die in a year, what would you change about how you live?

If you live that way now, you’ll know you lived the best life you could.

153. What’s the most essential part of a friendship?

What makes a true friendship last?

154. Would you like to be famous? (If yes, what would you want to be famous for? If no, why not?)

There are plenty of pros and cons to being famous.

10 First Date Speed Dating Questions

via: Pexels / mentatdgt

You don’t always have a ton of time to get to know someone on a first date. When you’re dealing with speed dating, that’s particularly true. In that situation, use these speed dating questions to find out if you’re compatible in just a few questions.

Here are 10 speed dating questions:

155. Do you follow politics?

One way or the other, you’ll want to be compatible on this.

via: Pexels / Element5 Digital

156. What movie could you watch over and over again?

If you hit it off, watch that movie together.

157. Do you speak any other languages?

If yes, get them to teach you a bit.

158. Do you see the glass half-full or half-empty?

Optimists and pessimists tend to work best when they’re together.

159. What do you like to do outside of work?

Find shared hobbies or activities you’d want to try together.

160. Have you read any good books recently?

Talking books can lead to real connection.

via: Pexels / Negative Space

161. What was your favorite game to play as a child?

Comparing childhoods is a great way to get to know one another.

162. What’s your death row meal?

If you have similar tastes, you know your first date night meal.

163. Do you have any claims to fame?

See their secret talent and learn a secret about them right off the bat.

164. What is your Myers Briggs type?

In an instant, you know if you are compatible.

Downloadable List of First Date Questions

Here is a downloadable list of good first date questions (right click the image and select Save Image As…):

More Great Questions To Ask

We have lists and lists of other questions that are perfect for any situation!

1. If you want to see what your date thinks about more complex subjects, check out our interesting questions to ask a girl.
2. If you’re generally at a loss for what to talk about, check out our simple post on questions to ask a girl.
3. To keep an already strong relationship interesting, questions for couples are a good place to look.
4. To understand the basics of getting to know people, check out our post on how to get to know someone: # of tips.
5. Starting a conversation can be hard if you don’t know how. We know how to start a conversation though.

How to Ask First Date Questions

Asking questions on a first date is scary. Just remember these steps and you’ll have a wonderful time.

Here is how to ask first date questions:

1. Be Yourself

The most important thing you can do on a first date is be yourself. And asking questions that you normally wouldn’t ask or answering them in ways that don’t agree with your character are two things you DO NOT want to do while on a first date. If you be yourself, she’ll either like you or she won’t and you’ll be fine either way.

2. Relax

(You’re getting to know one another. You’re both nervous and you both want this to go well. Realizing this will help you maintain your composure and able to chat more casually.

3. Have fun

You’re on a date with a girl you like. Make it fun for her by thinking up ways to make her laugh and being your best version of yourself you can be.

In Conclusion

Hopefully you’re now a little more prepared for your future first dates.

These first date questions will get the conversation going and all you have to do is keep it running smoothly.

Remember:  you’ve got this.