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Notice to all new readers: Girls, start with His Secret Obsession

Guys, you need The Obsession Method. Good luck :-)

First dates can be awkward, especially this day in age where people usually meet each other from an online site like Tinder or Bumble.

One of the best ways to alleviate the awkwardness is to ask each other funny questions and get a sense of each other’s humor and personality.

a girl laughing at a funny first date question

In addition to asking funny first date questions you can ask these myriad of different genre questions here. The top 100 funny first date questions are as follows….

Table of Contents

1. What was your first nickname?

This is a great question that requires more than a “yes” or “no” answer. Chances are it will be something goofy and silly that will reveal a bit about their childhood too and if they were a cranky or happy baby, whether they were an early talker, had a lisp, etc. Nicknames are always goofy.

2. What is the most embarrassing thing that has ever happened to you?

Embarrassing stories are always the funniest later on, once you’re over them of course. You can discover what your date is ashamed of and watch them blush and laugh. You’ll get a deeper understanding of their inner values in a humorous way.

3. What’s the worst joke you’ve ever heard?

Ever hear something so unfunny that you laugh? Like seeing something so ugly it’s cute? You can laugh over the stupidity of someone else’s joke.

4. What are some of the best pranks you pulled as a kid and an adult?

Delve into each other’s mind, see how their mind works with little tricks and manipulation. Pranks are fun if they’re harmless like ding dong ditch.

5. Have you ever drunk texted someone and how did it go?

Once again, embarrassing stories are always the funniest. But remember, it’s your first date so tell them about drunk texting a parent or grandparent, not your ex.

6. Who’s your favorite comedian?

Maybe you have the same favorite and can re-live the show with laughter or maybe you tell some of your favorite jokes and expose them to a new favorite comedian too. It’s a win win.

funny first date question can make dates a lot more fun

7. Show me your best accent?

Either they’ll do one super well that you’ll laugh because it’s spot on or they will be horrible and you’ll crack up. Both ways this one always ends in laughter.

8. What’s your guilty pleasure tv show?

Are they into reality tv, teen drama, etc. It’s a little secret that you both can tease each other about.

9. If you were a stripper what would be your stripper name?

When in doubt, this topic always makes people giggle. Keep it sexual and the attraction will bloom on the first date.

10. What is one of your freakiest fetishes?

Do they have a foot fetish or any type of fetish. It’s good to get it out there early on and keep it light as you get more comfortable in the relationship you’ll thank yourself for asking this early on.

11. Do you believe in ghosts?

Make some funny faces through your napkin and poke holes. That’s the truest test.

12. Do you think black cats are superstitious?

Do they believe in magic and bad luck? What other superstitions do they have? You can play some great tricks for later dates. And get some black cat ears for Halloween.

13. Do you think animals can understand you?

Do they talk to your animals in a telepathic sense? Or do they talk back? Experience the level of crazy you’re dealing with. Are they a cat or a song person… this can lead into more stories about childhood pets and the like.

14. Why are you single?

Everyone is asked that… what’s that crazy thing you do people can’t stand, or those absurdly high expectations? Or… is it just self-respect and a nasty dating pool?

boring questions can ruin a first date

15. Are you an early riser or a night owl?

Morning sex or night sex? Or both… a little dirty talk can lead to lots of giggles.

16. What’s your best tequila story?

Everyone has a tequila story… and usually they end in disaster. If they don’t have one make your first date unforgettable… or forgettable I guess.

17. What is your silliest fear?

Spiders? Ladybugs? Heights? Maybe you have the same one!

18. If you live to 99 would you rather keep your 25 year old mind or body?

Brains of looks?

What kind of person are you on a date with and do you want to pursue them based on what they choose? Are they physically or mentally stimulating (go for the later, it lasts longer).

19. What’s the craziest thing you have done out of boredom?

Prank call someone, stab someone’s tire? Teepee a house, lets hear the stories.

20. What is the cheesiest pick-up line someone has used on you?

Heat it and then use the same one back in a sexy accent. She’ll laugh, maybe with an eye-roll, but hey it’s still engagement.

21. What is one of your quirks?

What makes you unique? Nothing is sexier than confidence. Talk about the things that make you uniquely you, eyes bright and giddy.

22. What is your biggest pet peeve?

Is there something that just completely turns you off? Maybe it’s chewing while talking, breathing super loud, not saying please or thank you, being entitled or rude. Whatever it is get it out there so your date knows the expectations early on. You’ll probably end up sharing stories about annoying people and laughing about them.

23. What is your perfect utopia like?

As crazy as it sounds, what does a world you create look like? Are there dragons and unicorns? Or do people just give to give? Does money exist or is everything a barter system?

24. What’s something you like to eat that other people find gross?

Octopus? Alpaca? Alligator? What’s something you love that others turn their cheek from?

25. If you could be a the opposite gender for a day what would you do?

This is going to get some funny answers, anywhere from playing with genitalia to just being the sweetest or meanest with no punishment or reward.

26. Have you ever had a crush on your teacher?

Hehe, naughty time. Everyone has that hot teacher that they have an innocent crush on at some point growing up. Share your details.

27. If you were a boxer what would your nickname be?

Let’s see how creative you can get with each other.

28. If you only had 48 hours to live what would you do?

Make babies, swim, hike, write, take photos? The options are endless.

29. What is one of your weirdest talents?

What’s something you can do that not a lot of people can? Maybe you can make funny noises or roll your tongue weird… whatever it may be share away and show. Show and tell is a fun one.

30. Have you ever spit in someone’s food or drink?

During your waitressing days…. did someone ever piss you off enough for you to do this? What happened… spill your guts.

31. Have you ever gone pee in public?

Pulled over on the highway to pee? Who hasn’t?

32. Have you been arrested for being naked?

The best reason to be arrested, am I right?

33. What am I thinking about right now?

This is a cute one to ask that will obviously result in him or her thinking about their date.

34. What Halloween costume fits your personality best?

Cat? Elephant? Dog? Are you needy but distant like a cat? Emotional, large and sensitive like an elephant? Or playful and goofy like a pup?

35. Would you describe yourself as naughty or nice?

What side of Santa’s list do you fall under?

36. If you were a drink what beverage would you be?

Or would you be a shot? Sweet tea, lemonade, a margarita, a mojito… just to name a few.

37. If you had 5 dollars and some change at the dollar store what 5 things would you buy?

Let’s see those necessities. Candy? Toilet paper?

38. Tell me the stories about your tattoos and piercings.

Were you drunk or are they thoughtful and inspirational stories? Or are they just for fun?

39. What did you get detention for at school?

Were you perpetually late to school, did you skip class, beat up kids in the hallway?

40. Are eyebrows facial hair?

Food for thought…. Women have some pretty facial hair!

41. Are hotdogs sandwiches?

Yes… but I mean feel free to debate. See who can outwit who.

guy laughing at a hilarious first date question

42. Do you think dogs or cats have regrets?

Does your pet regret going home with you?

43. How many murders have you watched?

Just wait for that facial expression and then nervous or exorbitant laughter.

44. What’s your favorite comedy genre movie?

50 first dates, Elf, White Chicks. They’re all so good.

45. How many donut holes fit into your mouth at once?

The innuendos with this one…

46. Boobs or butt?

What kind of guy are you dealing with?

47. Is cereal soup? Why or why not?

Broth vs milk… the greatest debate.

48. What is a sexy name for a male and a female?

Then tell them that’s your middle name, just for giggles.

49. How do you feel about conspiracy theories?

Hear how crazy you sound to each other.

50. Which conspiracy theory should we start?

Then lighten it up and create your own! Bond over the silliness.

51. What is the weirdest fact you know?

Spill the beans… people are drawn to weird and eccentric.

52. What sport are you worst at?

Dodgeball? Basketball? Who hasn’t been attacked by balls?

53. What is something we all do as humans that looks ridiculous?

Brushing our teeth, dancing, peeing?

54. Pineapple on pizza?

The great debate made for every single human and a necessary first date question… do the two mix?

55. Does the toilet paper go over or under?

There’s only one right answer… is he or she neat or a slob?

56. What is the best cheese? Does it make you cut the cheese?

Bathroom jokes…. it doesn’t matter how old you are, they never get old.

57. What’s your best inside joke?

Share your favorite inside joke with each other, they might not even find it funny but it will be cute.

58. What’s the strangest thing a guest has done in your house?

Steal your food? Flirt with your then significant other?

59. Have you and your best friend ever fought over the same boy or girl?

Who hasn’t… but it was probably in middle school. Share the long ago lived gossip.

60. Have you ever used your looks to get out of a speeding ticket?

Perks of being a girl.

61. Have you ever flashed a cop?

Another perk of being a female…

62. What is the most annoying color?

Orange. It is most definitely orange, but go ahead and debate it.

63. What is your biggest cooking fail?

Have you had a dinner party and just completely ruined the recipes but served it not knowing? HOW EMBARRASSING. It is a devastating moment, but funny afterwards. Always try before you serve.

https://www.youtube.com/watch?v=YYFQ48-7f0o

64. What is your signature dance move?

Are you more of a salsa or shuffle type of woman?

65. If animals could talk, which would be the sweetest?

That is a thinker… boil it down to a couple and discuss.

66. If animals could talk, which would be the rudest?

What animal takes and takes and takes? Probably a human!

67. Are you accepting applications for a boyfriend/girlfriend?

Super cute and seemingly innocent question but clearly with ulterior motives.

68. Would you still talk to me if I walked like this?

Then do a funny penguin walk.

69. What was your dream job when you were little?

Maybe you accomplished it, or went even above and beyond. Some little kids want to be truck drivers but grow up to be architects!

70. If you won a trip for two to go anywhere in the world, where would you take me?

Bold, but hot.

71. Could you go for a week without your phone?

Hopefully you date a person and not the technology they are addicted to!

72. Did you ever skip school?

Ferris Bueller enjoyed his day off, you can too.

73. Do you snore when you sleep?

Huge deal breaker there, you know some couples sleep in different beds because of the snoring.

74. What’s something your parents do that makes you so so irritated?

Are they finger pointers, loud talkers, wild drunks?

75. What cartoon do you still like?

Guilty pleasure with that one?

76. If you could have a superpower what would it be?

Fly? Be invisible? Read other people’s minds?

77. What do you think you were in your past life?

Do you even believe in past lives? Maybe you were a bird, or an elephant or still a human just a different one.

78. Do you think your birth chart and zodiac sign define you?

Time to get crazy white girl on him.

79. Would you rather have more money or more time?

More money so you could use your time more wisely or more time to make more money… the choice is simple!

80. Would you survive a zombie apocalypse?

How are those survival tactics? Can you even start a fire?

81. Would you ever be on reality tv?

Or do people on reality television disgust you?

82. If you could be on the cover of a magazine which would you choose?

Vogue? People? National geographic?

83. What is the most irritating personality trait?

Cockiness… and a huge ego, or a little ego and self absorbed?

84. What’s something you wish you could forget but always remember?

It’s probably something super embarrassing to you but also extremely irrelevant to the rest of the world. Share it and then let it all go.

85. When was the best decade?

The 70’s or the now?

86. What’s the most embarrassing text you have sent?

Did you screenshot it and save it? I’m sure it would be hard to only choose one. Did you accidentally send your parents a nude?

87. Have you ever sent nudes? Send some to me?

Sneaky there…

88. What’s your go-t0 karaoke song?

Are you a country singer? That’s an easy go to genre for many,

89. Did you / do you have imaginary friends?

Are your friends you make in your head or are they real? Sometimes they are better up there.

90. What are most of your dreams about?

You… duh, most of my dreams are about the man or woman of my dreams which is clearly you.

91. 100 duck sized horses or one horse sized duck?

Do you love horses or ducks? Quality or quantity here…

92. Would you rather control space or time?

Why not both?

93. What is your favorite joke?

Knock knock…

94. What kids movie scares you?

Monsters Inc. for sure… but cuddles later with the kids classic is always nice.

94. What’s your life slogan?

Life is hard and then you die, carpe diem… is that glass half full or half empty?

95. Want to play two truths and a lie?

ALWAYS a classic and a winner.

96. Want to play truth or dare?

Always so goofy on the dares. Can dare for a kiss too.

97. What’s your favorite fantasy?

You and me. Or something less cheesy works too.

98. Am I your usual type?

There isn’t really a right answer for this but it’s funny because people really are pretty shallow with looks.

99. Describe your funniest memory in explicit detail.

The classic, retelling the funniest memories with every single detail emphasized. Nothing is funnier than watching someone relive their funniest memory because the joy that lights up the entire room and aura is absolute magic.

You only get one first date with every person you meet, you only get to make a first impression once, so make it good with these 100 funny first date questions.

They’re light but also go beneath the surface and you can really discover the way someone thinks through their sense of humor.

If you end up making the man or woman your significant other 50 hot questions to ask your girlfriend can be found here.


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As a young man, you need to master 3 areas of your life: Health, Wealth and Sex.

Here's how:

Health: Okinawa Flat Belly Tonic [Video]

Wealth: The Fast Tracks Webinar

Sex: The Obsession Method [Kate Spring]

Easy!

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