Fun Questions to Ask a Guy (That Open Up His Playful Side) post image

Fun Questions to Ask a Guy (That Open Up His Playful Side)


Conversations have a way of becoming quite dull- maybe it’s because the art of conversation has mostly been lost in the digital age of hiding behind our screens and communicating via gifs and emojis.

Asking the right questions is a powerful way to galvanize a conversation and create a connection. These fun questions cover a range of topics and are great for asking a guy you like, a guy you’re dating, a friend, a co-worker, anyone really!

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

Some questions will reveal shocking information that may surprise you, some will bring out a hilarious story or maybe an embarrassing moment, some may open the door for deeper conversations.

Either way, they will steer you into interesting new directions.

MORE: 300 Conversation Starters (Rejection Proof)

    • What do you think will finally break the internet?
    • Who would play you in a movie of your life?
    • What was the most cringe-worthy movie you’ve ever seen?
    • If your life was a reality show, what would the premise be?
    • What is the worst fashion trend you’ve ever taken part in?
    • What is your most random pet peeve?
    • What is a food most people love that you hate?
    • What is the first law you would change if you were president?
    • What movie do you quote most often?
    • What is your all-time favorite song lyric?
    • What was your biggest childhood fear?
    • What would your younger self be disappointed in about your adult self?
    • What is the stupidest cliche expression everyone uses?
    • Which TV character do you most relate to?
    • What song would be featured in the soundtrack of your life?
    • What is the dumbest thing you’ve ever purchased?
    • If you inherited a billion dollars, what would you buy first?
    • If you had to give up one body part, which would it be?
    • What has been your worst kitchen disaster?
    • Has a commercial ever made you cry?
    • What do you think about girls who filter every photo they post?
    • Is social media ruining society?
    • Would you rather never have to do the dishes for the rest of your life or the laundry?
  • If you could get a definitive answer to one question, what would it be?
  • Do you believe in any conspiracy theories?
  • What is a useless topic you know a lot about?
  • Do you have any hidden talents?
  • What is one job you would be awful at?
  • What is your favorite curse word?
  • Would you rather make your internet search history public or your bank balance?

MORE: 50 Great Questions To Ask A Guy

A Few Things to Keep In Mind:

Remember, the point of a conversation is to discover someone, not to impress them. If your goal is to impress or win them over, you’re doing it wrong.

This article can be used as jumping off point to have some fun and funny conversations, but you need to be coming from the right mindset. This means you aren’t needy and aren’t looking for ways to gain validation. You aren’t concerned with protecting your ego and trying to come across a certain way.

Being good at conversation really comes down to being genuine. Most people can see right through a fake facade and it’s off-putting. So just be real, be confident, be yourself, and have fun with it.

I hope this article gave you some fresh ideas for funny questions to ask a guy or anyone else. If your focus is on building a connection with a guy, there are two important moments you need to be aware of. The first is that at some point In your relationship, your man will start to pull away. You may notice him becoming more distant and less engaged. It seems like he’s losing interest in you and you worry that soon he’s going to just leave. Do you know what to do to get things back on track? If not, read this next: If He’s Pulling Away, Do This...

The next issue arises at that inevitable point when the man asks himself: Do I want to commit to this woman for the long term? The answer will determine everything. Do you know what makes a man see a woman as girlfriend/wife material? Do you know what inspires a man to commit? If not, you need to read this too: The #1 Things Men Desire in a Woman

Want more great questions? Check out these articles:

425 Amazing Truth or Dare Questions

425+ Never Have I Ever Questions: The Ultimate List

20 Cute, Amazing Question to Ask a Guy You Like

Fun Questions to Ask a Guy to Get to Know Him Better

Funny Questions to Ask a Guy or Girl

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you...

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