20 Questions

Very Funny Flirty Questions to Ask a Girl

Playful and humorous questions that create chemistry, make her laugh, and show your fun side while building attraction.

1

If you were a pizza topping, what would you be and why?

Click to see why this works

Why this works

Silly and unexpected, this question is playful while revealing her personality and sense of humor.

2

What's the most ridiculous thing you've ever done to impress someone?

Click to see why this works

Why this works

Shows vulnerability and humor while creating a fun, slightly embarrassing story to bond over.

3

If you could have any superpower, but it only worked when you're around me, what would it be?

Click to see why this works

Why this works

Flirty and creative, this question shows interest while being playful and imaginative.

4

What's the weirdest compliment you've ever received?

Click to see why this works

Why this works

Funny and light, this opens up conversation about compliments while showing you're interested in what others think of her.

5

If we were both characters in a rom-com, what would our meet-cute be?

Click to see why this works

Why this works

Romantic and creative, this question lets her imagine a fun scenario with you while being playful.

6

What's the most embarrassing thing that's happened to you on a date?

Click to see why this works

Why this works

Shows you're comfortable with vulnerability and creates a fun, relatable conversation about dating mishaps.

7

If you could only eat one food for the rest of your life, what would it be? (And yes, I'm judging your answer)

Click to see why this works

Why this works

Playful and judgmental in a fun way, this creates a light debate while being silly.

8

What's the most ridiculous thing you believed as a kid?

Click to see why this works

Why this works

Childhood stories are always funny and endearing, showing her innocent side while being relatable.

9

If you had to describe yourself using only emojis, what would they be?

Click to see why this works

Why this works

Modern, fun, and creative, this lets her express herself in a playful way while being interactive.

10

What's the worst pickup line someone has ever used on you?

Click to see why this works

Why this works

Funny and shows you're confident enough to laugh at pickup lines while learning what doesn't work.

11

If you could be famous for something completely ridiculous, what would it be?

Click to see why this works

Why this works

Silly and imaginative, this question lets her be creative while being funny and light.

12

What's the most random thing you've ever Googled?

Click to see why this works

Why this works

Relatable and funny, everyone has weird Google searches, and this creates a light, humorous conversation.

13

If you could have a conversation with your pet, what's the first thing you'd ask them?

Click to see why this works

Why this works

Cute and funny, this shows her caring side while being playful and imaginative.

14

What's the most ridiculous rule you had growing up?

Click to see why this works

Why this works

Relatable and funny, childhood rules are often absurd and create bonding over shared experiences.

15

If you could make one thing socially acceptable that currently isn't, what would it be?

Click to see why this works

Why this works

Funny and thought-provoking, this lets her be creative while showing her personality and sense of humor.

16

What's the weirdest dream you've ever had?

Click to see why this works

Why this works

Dreams are often bizarre and funny, creating an entertaining conversation while being personal but not too intimate.

17

If you were a villain, what would your evil plan be?

Click to see why this works

Why this works

Creative and playful, this lets her be imaginative while being funny and showing her personality.

18

What's the most ridiculous thing you've ever bought online?

Click to see why this works

Why this works

Relatable and funny, online shopping stories are often entertaining and create bonding over shared experiences.

19

If you could have dinner with any fictional character, who would it be and why?

Click to see why this works

Why this works

Creative and fun, this reveals her interests while being playful and imaginative.

20

What's the most random skill you have that most people don't know about?

Click to see why this works

Why this works

Interesting and personal, this reveals something unique about her while being fun and surprising.

The Art of Flirty Humor

Expert tips and techniques for getting the most out of these questions.

Making Her Laugh and Feel Attracted

Read the Room

Pay attention to her responses and energy. If she's not laughing or seems uncomfortable, switch to lighter topics.

Be Playful, Not Mean

Teasing should be light and fun, never hurtful. The goal is to make her laugh, not feel bad about herself.

Share Your Own Funny Stories

Reciprocity is key. Share your own embarrassing or funny moments to create a balanced, fun conversation.

Building Chemistry Through Humor

The Ice Breaker Sequence

Start with silly, non-threatening questions
Build on her responses with follow-ups
Share your own funny related stories
Keep the energy light and playful

The Vulnerability Builder

Ask about embarrassing moments
Share your own funny failures
Create inside jokes together
Build connection through shared laughter

The Creative Connection

Use hypothetical scenarios
Ask imaginative questions
Build on each other's ideas
Create a fun, collaborative conversation

Common Pitfalls to Avoid

Don't Overdo the Teasing

Too much teasing can come across as mean or immature. Balance humor with genuine interest and compliments.

Avoid Inappropriate Humor

Keep jokes clean and appropriate for the setting. Off-color humor can quickly kill the mood and make her uncomfortable.

Don't Make Everything a Joke

While humor is great, also show genuine interest in her as a person. Ask some serious questions too.

Further Reading

"The Art of Seduction" by Robert Greene
"Models" by Mark Manson
"The Charisma Myth" by Olivia Fox Cabane

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation