Men Love Humor: Funny Questions to Ask A Guy & Warm His Heart!

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You spend hours getting ready for the date: make-up, hair, choosing your outfit, choosing shoes, then re-doing all of everything.

You stress about it, are nervous about it, and ultimately, you can’t stop thinking about it—stop!

But did you ever stop to think of the importance of being funny?

Yes, it’s great to be excited and a little bit nervous at the beginning of a relationship but it’s not completely necessary.

Knowing funny questions to ask a guy is important because it means you will be prepared and not feel nervous about what to say.

The ultimate goal here is let your true personality shine through and be as comfortable as possible because, at the end of the day, the sound of laughter is one of the foundations of every relationship.

Just like getting along with one another and truly feeling happy with one another’s company. The best way to do that? Don’t be afraid to be silly, crack a joke, and just be yourself

Laughing together or finding one another funny can help you improve the experience you have with him. Even though an idea of humor can be different from one person to another, it doesn’t have to stop you two from finding common ground.

These funny questions will help you find common ground!

Not only is laughter and being humorous a great place to just enjoy one another, it’s always a strong connection that you two can use to help develop your bond.

All it takes is a joke or a question and you both will be laughing in fits on your way to a great relationship. 

“Being Funny” might look like different things to different people but ultimately, it shouldn’t be difficult. The priority here is to test the waters in figuring out what kind of humor the other person has.

For example, the fact that Caroline wore a pair of plaid shorts with her striped shirt probably won’t make him laugh, even though it might send your girls into a fit of giggles. Find that sweet spot and keep tickling it!

Here are a few examples of funny questions you can keep with you to keep the laughter going.

Funny Questions Suggestions

  • What would be the craziest thing you would buy or do if you won the lottery?
  • What’s the most cringe-worthy experience you’ve ever had?
  • If you were arrested tonight and called your friends tomorrow, what would they think you got arrested for?
  • What’s the most insane thing you would do? For how much money?
  • Do you have any weird family members?
  • What’s the stupidest celebrity name you’ve ever heard?
  • If you had one outfit that you had to wear for the rest of your life what would it be?
  • Which job would be the worst job ever?
  • What’s the most awkward thing a girl has ever done to you?
  • Have you ever been pranked or have pranked anyone?
  • What’s the grossest thing you have ever done or seen?
  • With whom would you never hook up?
  • If you had to be the most annoying and obnoxious person in the world right now, what would you do?
  • What’s your favorite comedy movie?
  • Do you know any funny jokes?
  • If you owned a yacht in the future what would you name it?
  • If you were fighting with him, what would be the most ridiculous way to settle the argument?
  • If you had to choose, would you rather live in a nudist colony or be celibate for life?
  • Right now, what’s the silliest fashion trend you’ve seen?
  • What is one of the craziest fashion trends that women love but you hate?
  • If you hated your job and wanted to leave, what would be the best way to quit?

I hope that these questions will help you keep the conversation going and move on from there!

Always keep them with you in case you run out of things to say and are looking for a good time!