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138 First Date Conversation Starters – Keep things fun and lighthearted.

138 First Date Conversation Starters – Keep things fun and lighthearted.

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First dates are always nerve-wracking, so something tells us you could use some tried-and-tested first date conversation starters.

With these first date questions up your sleeve, you will never be lost for words and will never wonder how to start a conversation again!

Contents

20 Best First Date Conversation Starters

Ready for the big guns? Let’s jump right in!

Here are the 20 best first date conversation starters:

1. What’s the best present you ever gave someone?

Just so you can manage your expectations.

2. What’s the worst pickup line you’ve ever heard?

Hopefully, it’s not the one they used on you!

3. What sorts of things make you laugh out loud?

It’s always nice to find out that you and your (potential) significant other share a sense of humor — it makes things so much easier.

4. What is something you wish you did more of in your life and something you wish you did less of?

Priorities matter — you don’t want to end up with someone whose values are very different from yours.

5. Where is the most fun place around where you live?

Who knows, you might go there on your second date!

6. What’s your go-to funny story?

Chances are they will tell it to you anyway, and it’s probably not quite as funny as they think — so you might as well get it over with.

7. What do you like most about living here?

With any luck, it should be the fact that you live here as well.

8. What’s on your bucket list?

You could cross out some of the items together!

9. What’s expensive but totally worth it?

You know what they say: there’s nothing more expensive than cheap things.

10. When do you feel most out of place?

We all feel like impostors every now and then.

11. How did you meet your best friend?

That should make for a cute story.

12. Describe your perfect day.

Take note of the answer, and make it happen one day.

13. What’s something I’d be surprised to know about you?

People are full of surprises!

14. What’s the most important thing for you?

If it’s not something along the lines of love, friendship, or family, you might want to reconsider going on a second date.

15. Where did you grow up?

Childhood stories are one of the best ways to get to know someone better.

16. Is there a place in this world that makes you feel like home?

We all have one.

17. What’s your favorite place to go to around town?

And how about you go there together?

18. Do you have any pets?

You want to know if they are a cat or a dog person!

19. How do you spend your free time?

That can tell you a lot about a person.

20. Tell me about your work.

Most of us spend two-thirds of our waking hours working, so it’s one of the most important aspects of our lives.

19 First Date Conversation Starters with Your Crush

It’s difficult to find the right words when you really like someone. Don’t worry, we’ve got you covered with our list of conversation starters with your crush.

Here are 19 first date conversation starters with your crush:

21. What’s something I wouldn’t guess about you?

If you think that people are “what you see is what you get,” you might want to think again.

22. What does a typical day look like for you?

How we spend our days is how we spend our lives.

23. What kind of person are you looking for?

Who knows, you might be just their type!

24. What nicknames have you had throughout your life?

Childhood nicknames always make for a good laugh.

25. What really cheesy song do you love?

Ah, we all have that song we like to sing in the shower or on boozy karaoke nights.

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

A last-minute trip abroad? A one-night stand? Quitting a job on a whim?

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

Our bet would be to go through hard times together.

28. What small things brighten up your day when they happen?

The secret to happiness is enjoying the little things in life.

29. Describe the best night of your teenage life.

That should make for a funny story!

30. What do you like to do for fun after a busy workday?

Some people like to go out and have a blast, while others prefer to Netflix and chill.

31. Are you a chocolate lava cake or a savory crepe?

That’s a tough choice!

32. What are your passions?

Someone’s passions and interests tell you a lot about where their real values lie.

33. What do you hate most about first dates?

That knot in your stomach? The awkward pauses? The fact that you always seem to get your clothes stained regardless of what you eat? It’s hard to pick just one.

34. What is your guilty pleasure?

Late-night ice cream? Cheesy rom coms? Readying celebrity gossip on your lunch break?

35. Do you have any pet peeves?

Take our word for it: if you share the same pet peeves, this might very well be a match made in heaven.

36. How was your day?

Very few people ask that question and actually mean it. Don’t be one of them — and not just on first dates.

37. Do you like to travel?

And would they be up for a romantic getaway any time soon?

38. Tell me more about yourself.

You’d be surprised by just how much people are willing to share on a first date.

39. What’s your go-to drink on a night out?

Are they a tequila or a pina colada person? Or a good old beer is more their thing?

17 Funny First Date Conversation Starters

Want to lighten up the mood? Funny conversation starters are the way to go.

Here are 17 funny first date conversation starters:

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

What? Toasters can be evil incarnate.

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

The creativity of phone pranksters never ceases to amaze.

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

And how much time do you waste on it every day?

43. What household chore is just the worst?

Cleaning the bathroom, for sure.

44. What fad did you never really understand?

Cross-body manbags? Wearing sandals with socks?

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

If they say “Being productive,” there’s something seriously wrong with them.

46.. What’s the worst date you have ever been on?

Let’s hope you can do better than that!

47. What do you hate the most about dating?

The expectations? The pressure to show yourself in your best light?

48. If you had a robot for a day, what would you want it to do?

Imagine if we had robots that could deep clean your house.

49. If you could have an endless supply of any food, what would you get?

Ice cream or pizza?

50. If you could choose your age forever, what age would you choose, and why?

Surprisingly, not everyone wants to be forever young.

51. If Morpheus offered you the blue pill and the red pill, which one would you take?

That’s a hard one.

52. What did you think was so cool that you found out was lame later?

How about driving around with the music blasting and your car windows rolled down?

53. What’s your guilty pleasure TV show?

Keeping Up with the KardashiansJersey Shore, or The Only Way Is Essex?

54. What’s your least favorite fruit?

Who even buys pomelos? And don’t even get us started on sour cherries.

55. What was your worst fashion disaster?

Those jeans probably seemed like a good idea at the time.

56. If you could be any Disney villain, who would you be?

Maleficent seems pretty cool.

57. What commercial jingle gets stuck in your head all the time?

Be prepared to get it stuck in your head too!

18 Fun First Date Conversation Starters

Make your conversation with her exciting with these fun questions to ask.

Here are 18 fun first date conversation starters:

58. Are you more of an indoors or an outdoors person?

Or a bit of both?

59. What’s your favorite international food?

How much time do you have?

60. What are your favorite alcoholic and non-alcoholic drink?

Yes, coffee counts.

61. What odd talent do you have?

If they can wiggle their ears, they are a keeper.

62. Would you like to start a hobby?

And what would it be?

63. What is your most desired travel destination?

Who knows, you could end up going there together one day.

64. What would you like to be known for?

Having a special talent? Inventing something? Helping others?

65. Tell me about the best vacation you’ve ever taken.

Just don’t pick one you had with your ex!

66. What do you have lined up on Netflix?

Do you have the popcorn ready?

67. If you had the ability to read minds, would you?

That should be quite sobering.

68. If you could hop on a plane right now, where would you go?

Ah, where do we even start?

69. If you could sit front row at a concert, which one would you go to?

That should give you an idea or two for birthday and Christmas presents.

70. If every job paid the same, what job would you do?

The options are literally unlimited.

71. If you had a theme song, what would it be?

Life would be so much better with a soundtrack.

72. What would you do if you won the lottery?

Travel the world? Buy a sports car? Build the house of your dreams?

73. What’s the one thing that you wish you had invented?

If you had come up with the iPhone, we’d be having a very different conversation right now.

74. What was the first concert you ever attended?

It’s okay — we all had a questionable taste in music growing up!

75. If you could trade lives with one person for an entire day who would it be, and why?

The Queen of England? Beyonce?

18 First Date Would You Rather Conversation Starters

Would you rather questions make some of the best ice breakers on your date! This is a fun way to get know them better too.

Here are 18 first date would you rather conversation starters:

76. Would you rather find your true love or a suitcase with five million dollars inside?

Love is the most important thing in life, but five million sure sounds tempting.

77. Would you rather never lose your phone again or never lose your keys again?

Well, phones are more expensive to replace, aren’t they?

78. Would you rather be able to be free from junk mail or free from email spam for the rest of your life?

We’d pick email spam, any day.

79. Would you rather be completely invisible for one day or be able to fly for one day?

Being able to fly must be awesome, but won’t everyone stare at you?

80. Would you rather live on the beach or in a cabin in the woods?

And what would your days look like?

81. Would you rather be famous but ridiculed or just be a normal person?

Being a normal person is very underrated.

82. Would you rather never be stuck in traffic again or never get another cold?

Health is more important, but traffic jams are extremely annoying.

83. Would you rather be balding but fit or overweight with a full head of hair?

In either case, you should love yourself as you are.

84. Would you rather be beautiful/handsome but stupid or intelligent but ugly?

Is that even a question?

85. Would you rather be able to teleport anywhere or be able to read minds?

We’d go with teleporting — people’s minds are full of nasty thoughts.

86. Would you rather travel the world for a year on a shoestring budget or stay in only one country for a year but live in luxury?

Depends on the country.

87. Would you rather have all your clothes fit perfectly or have the most comfortable pillow, blankets, and sheets in existence?

A comfy pillow is more difficult to find that the Holy Grail.

88. Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?

It depends. How good of a singer are you?

89. Would you rather have unlimited international first-class tickets or never have to pay for food at restaurants?

Well, you can only have so many trips abroad in a given year, but you can easily eat three or more times in a restaurant every single day.

90. Would you rather go back to age 5 with everything you know now or know now everything your future self will learn?

Who in their right mind would choose to go through puberty again?

91. Would you rather be able to see 10 minutes into your own future or 10 minutes into the future of anyone but yourself?

Both sound like pretty a bad idea.

92. Would you rather be married to a 10 with a bad personality or a 6 with an amazing personality?

Remember, looks don’t last forever.

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

Although it’s best to be right on time.

14 Interesting First Date Conversation Starters

Want to start off the conversation with your date on the right foot? These interesting conversation starters should get the job done.

Here are 14 interesting first date conversation starters:

94. If you could have lunch with any celebrity in history who would it be?

Now that is what we call an interesting date!

95. Who is your favorite YouTuber?

You might end up subscribing to their channel yourself.

96. Who are you embarrassed to admit you follow on Instagram?

Come, now — we all have our dirty secrets.

97. What’s the best meal you’ve ever had?

If things go well between you two, you could try cooking it for them one day.

98. Who is the most bizarre person you’ve met?

There are some truly weird people out there.

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

We’d probably waste it on social media and funny cat videos.

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

That should be an interesting story!

101. What are some movies you really enjoyed?

You could end up with some awesome movie recommendations!

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

This one is not for the faint-hearted.

103. If you could give me a tour of your hometown, where’s the first place you would take me?

That should make for a truly special date.

104. What business would you open if you knew you wouldn’t fail?

A fancy chocolate shop? An antique bookstore? A scuba diving school?

105. Are you stuck on a certain TV show right now?

Aren’t we all?

106. Do you have a favorite film or film genre?

If you have the same taste in movies, you two might be a really great match.

107. What did you name your first car?

Let’s face it: we all had a cute nickname for our first car.

13 Random First Date Conversation Starters

There’s nothing like random conversation starters to make people feel more at ease.

Here are 13 random first date conversation starters:

108. What’s the best pet name you can come up with?

No, Rexy just doesn’t cut it.

109. What is the best room in your house?

It’s usually the one with the most natural light.

110. What animal or insect do you wish humans could eradicate?

Has got to be cockroaches.

111. What do you think of tattoos?

Remember, tattoos are not a personality trait.

112. What was the last funny video you saw?

And how about we watch it together?

113. What do your Saturdays usually look like?

We bet they’d look a lot better with you around.

114. Did any of your former classmates end up becoming famous?

And are you jealous? Not even a little bit?

115. What fact floored you when you heard it?

Apparently, honeybees can be trained to detect bombs.

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

We know we don’t take it too well.

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

Drunk figure skating would make for quite the spectacle.

118. Have you ever joined any meetup groups?

And did you actually go to some of the meetings?

119. What’s your favorite season?

All seasons are special in their own way, but it’s always nice when you and your partner share a favorite.

120. What kind of phone was your first cell phone?

This one is bound to make you both feel ancient!

18 Deep First Date Conversation Starters

Ready for the heavy artillery? Then make sure to give some of our deep conversation starters a try.

Here are 18 deep first date conversation starters:

121. What’s something that comes easier to you than it does for most?

Sleeping counts too!

122. What’s been the most significant or best year of your life so far?

That should send them on a trip down memory lane.

123. Where is ‘home’?

In a loved one’s smile?

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

And what made it so special?

125. What do you do to unwind?

Do you like to go there alone or with company?

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

That should be interesting!

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

You can have your very own book club for two.

128. What is the weirdest scar you have, and how did you get it?

We’ve all been a little too wild for our own good at times.

129. What makes you feel sentimental?

Who doesn’t get teary-eyed every now and then?

130. What are 5 things you want to accomplish before you die?

Don’t put them off for too long!

131. Are you good at keeping secrets?

The thing is, everyone says they are — and then they go on and spill the tea.

132. Where would you never, ever move to, even for the job of your dreams?

There’s more to life than money or a great career.

133. What’s your earliest memory of feeling wonder?

That’s something you should never forget.

134. Who has been the most influential person in your life?

And why?

135. Do you have any regrets in life?

It’s okay to have some, but don’t dwell on them too much. We can’t change the past.

136. What’s the most rebellious thing you’ve ever done?

Hey, we’ve all had our crazy teenage years!

137. Where do you see yourself in 10–15 years?

And are you now where you thought you’d be ten years ago?

138. Do you consider yourself an introvert?

In any case, you are great as you are: introverts and extroverts both have their superpowers.

Downloadable and Printable List of First Date Conversation Starters

Here is a downloadable and printable jpg/pdf list of first date conversation starters (right-click and select Save Image As…):

More Awesome Tips to Start a Conversation with Anyone

Would you like some more tips on how to start a conversation with anyone? We have plenty!

  1. Check out our extra-long list of personal questions to ask anyone.
  2. Then, take a look at our favorite questions to ask a girl over text.
  3. Finally, read our selection of the best would you rather questions clean.

How to Pick the Best First Date Conversation Starters

There’s no two ways about it: first dates are hard. It can be difficult to start a conversation with someone you really like — especially if you don’t know them very well (or at all!).

Need some help?

Here’s how to pick the best first date conversation starters:

1. Use Something the Other Person Has Said as a Starting Point

The best way to come up with a great conversation topic is to use something your date has just said as an inspiration. Did they share something about their personal life? Their hobbies and interests? Their job?

Whatever it is, simply ask them a follow-up question and take it from there. Most people love talking about themselves!

2. Don’t Worry About Being Too Original

First dates are hard enough as it is. There’s absolutely no need to put extra pressure on yourself to come up with wildly original or intellectual conversation topics. It’s perfectly fine to keep things fun, simple, and lighthearted.

Plus, your date is probably just as nervous as you are! The chances are that they will be too worried about making a great first impression to pay attention to how original your conversation starters are.

3. Just Go with the Flow

All great conversations have a certain natural rhythm to them. For best results, don’t try to force things too much and simply go with the flow. Listen to what your conversation partner is saying and respond as genuinely as you can. Authenticity makes for the best conversations.

In Conclusion

Did you enjoy our selection of first date conversation starters? We hope that you will put them to good use — and that they will lead to a second (and a third!) date!

About The Author

Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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