40 Cute and Funny Questions to Ask a Guy

There are a wide array of questions you can ask a guy you’re interested in. Asking these questions will not only give you a gateway to his mind. They also serve as a way to open him up to you. Some are strategic methods to open his heart. Remember asking questions can not only work as ice breaker, but they can also get the guy more involved into the conversation.

10 Funny Questions to Ask a Guy

To ease any guy into opening up to you, it’s good to make him laugh. He will begin to relax and become friendly towards you. These questions are designed to make his easy going side shine through. He’ll probably be surprised that you’re asking some of them but will appreciate the gesture. You’ll boost his mood most likely and he’ll associate good feelings with you. Playful and engaging questions make for a memorable experience for the both of you.

1: What moment sticks out for you as your most embarrassing experience ever?

2: What is your quirky pet peeve?

3: Are you of the naughty or nice variety?

4: What celebrity do you have a secret crush on?

5: What would be the one meal you could eat every single day and never get bored?

6: Have you ever been caught in your birthday suit accidentally?

7: What is the most hilarious childhood memory you can think of?

8: Cutest animal on the planet?

9: Can you remember the funniest thing you ever did or said?

10: If you were a server, would you spit in a customer’s food for being rude to you or someone else you work with?

10 Questions Guys want you to Ask

These questions are things that a guy can relate to. They are thought provoking and make him conjure up ideas that perhaps he hadn’t previously asked himself. He’ll feel a sense of excitement as he ponders the questions you ask. You show him your playful side and give off the vibe that you have an idea on how a guy thinks. Maybe you don’t but he’ll know you care about what he cares about which is a huge bonus to him. Some of the questions will throw your potential guy for a loop and he’ll appreciate your spontaneity and flirty nature. You’re busting into his intellect when you ask questions like these. It shows your smart side.

1: If you had to choose an athlete to practice with, who would it be?

2: Are you able to go to the Victoria’s Secret website and choose two pieces of lingerie you’d love to see on a woman like me?

While this question may seem risky, you’ll get a lot out of his answers. For example, if he chooses something in red then he wants to see your wild side. This also opens him up to romance with you.

3: What would you say to your President if you ran into him randomly?

4: If you won a trip to go anywhere on earth, where would you take me?

5: Can you think of a movie title that best explains your life currently?

6: Who is your best friend and how long have you known him/her

7: Who would you have lunch with if you could choose anyone whether living or not?

8: What is your current goal at the moment?

9: What do you feel is the world’s biggest problem right now?

10: What is your favorite thing to wear to bed?

10 Ways to Really Get to Know Him

These questions allow you to analyze how your guy feels about himself, his ideas and views of the world. It’s hard to get someone to open up, especially men but with these questions you can get an indication of who they are. For example, the first question is about what they would choose as their super power. If they say they’d like to stop time, this indicates that they might feel unprepared often. If they say they want to be invisible, he has often had times in life where he’s been mentally attacked. You can figure out what his dreams are without asking that specific question. These are still questions to warm him up.

1: What would your preferred super power be?

2: If money was no object, where would you live?

3: Smart or happy? What is more important to you?

4: Would you rather ask permission with the risk of someone saying no or beg forgiveness later?

5: Are there things you are superstitious about?

6: What do you think people would say about you? Nicest things? Worst things?

7: What do you feel are your weaknesses?

8: What are you earliest memories?

9: Name the coolest place you went with your parents and what you did?

10: What was your worst job and why?

10 Romantic Questions to Up the Ante

Now that you’ve warmed him up with the previous questions, you can start asking him about romance if it feels right. They are not direct questions about the romance between you and him. They are more indirect and allow him to contemplate where he sees things going with you. You may be bridging the relationship gap with these powerful love buzz questions. You also get inside his head to find out if he’s really the right guy for you.

1: How old were you when you had your first kiss and what was it like?

2: Do you lead your life with your heart or your head?

3: Have you ever experienced a major heartbreak in a romantic relationship? Details?

4: What do you feel is the cutest part about yourself? Physical and mentally?

5: What would you say is your idea of romance?

6: What part of the female body are you most attracted to?

7: Do you prefer candlelit dinners at home or a fancy restaurant setting?

8: What is your ideal romantic night?

9: What are you thoughts about Valentine’s Day?

10: Which would you be? Guy who sends a bouquet from the flower shop or handpicked wild flowers you deliver yourself?