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Dating 101: Quirky and Fun Questions to Ask Your Boyfriend

Fun Questions To Ask Your Boyfriend
Need something totally random to do when you meet your boyfriend next? Try asking him some fun questions to while away time, and in the bargain get to know his deep, dark and dirty secrets.
Buzzle Staff
Last Updated: May 31, 2018
Fun question to ask
Relationships can reach a point when suddenly you realize you have nothing to talk about. Relax girls, it's not the end of the world. Happens to everyone. The best thing you can do is use this absence of interesting conversation to ask some totally random but fun questions to your boyfriend.

You'll have some light-hearted fun, and may even get to know things about him you never knew (or wish you never knew). Here's a bunch of such questions you can use.
Fun Questions You Can Ask Your Boyfriend
Did you ever have a crush on your teacher or someone much older when you were a kid?
  • What was your first impression about me?
  • How close am I to that first impression?
  • If you were a fictional character who would you be?
  • Which is the song you associate with my image?
Have you ever committed a petty crime?
  • If I caught you lying to me, how would you save yourself?
  • What is your wildest fantasy?
  • If you could give up one of your senses, which one would it be? Why?
  • What would be the first thought to come to your mind if someone told you that they saw me with another guy?
Father and Son time
  • What is the wackiest gift you have ever received or given someone?
  • Which female celebrity would you want to take away for a weekend?
  • If you could get one superpower, what would it be?
  • If I were a fruit, what would I be?
Hip hop funk dancer dancing man
  • If you were given a chance to give up all but 3 things to have a whole new, more successful life, what are the 3 things you wouldn't give up?
  • The most embarrassing thing someone has ever said or done to you is?
  • Have you ever fantasized about a friend's girlfriend?
  • What was the craziest thing you've done on a dare?
  • What's the most ridiculously expensive gift you gave someone?
  • Your worst date. Describe it.
  • Everyone had a crush on a TV character when they were teenagers. Who was yours?
  • If you could be invisible for a day, who would you want to spend it with?
Blank red book on white.
  • Lights on or off?
  • If you had to describe our relationship in 5 words, what would they be?
  • Have you ever lied about something and pacified yourself by saying it was for a 'greater good'? When? What? How?
  • If I were to be your slave for a day, what would you ask me to do for you?
  • If you could be a woman, who would you want to be?
  • What do you think women find most attractive about you?
  • Who do you think is the sexiest of my friends?
  • If I told you that I had a dream that I cheated on you with your best friend, how would you react?
Well, that list should easily help you get through at least a few evenings of nothing-to-do-ness. You can tweak the questions as you please and even come up with your own to add to the list and watch as your boyfriend squirms and blushes at some, avoids some like the plague and is genuinely flabbergasted at some. Just remember, they're all in jest. Don't turn it into an interrogation. Have fun!