Cheeky Questions To Ask A Guy (That Anyone Can Use)

Sometimes it is hard to know just what to say when you are getting to know someone, especially if you think that you might really like them. This is especially the case if you haven’t really spoken to the (young) man before, and you really want to make an impression upon him.

You can ask flirty, dirty, random, funny, deep, or awkward questions. I personally like cheeky questions (cheeky, meaning forward, bold, pert, brazen), without being stupid, overtly sexual, or prying too early on in getting to know a guy.

I Hate The Old Stuff

When I am first chatting up a guy, I try not to rely on the old standby conversation starters that I think are pretty darn overdone (and boring):

  • Have I seen you here before?
  • Do you work out?
  • Do you have a girlfriend?
  • Why don’t you tell me more about yourself?
  • Do you come here often?

And then there are the ones I’ve seen on other sites that I can’t BELIEVE other people recommend you actually use, like:

  • Why’s your type?
  • How can you be single?
  • Anything about sex (whaaa?)
  • Do you prefer cuddling or making out (huh, really, people ask that?)
  • What do you find hot in a girl?
  • What do you wear in bed?
  • Do you fancy me?

Maybe I’m old fashioned, or maybe I’m just old. But I can’t possibly imagine asking any of the questions above if I was genuinely interested in a guy I was talking to.

When you are first talking to a guy, not only are you trying to learn about this person who you think is physically attractive, but you are also trying to communicate good things to him about yourself as well. If you ask really boring questions, or questions that you don’t even really seem interested in getting the answer to, you aren’t doing much to put your best foot forward at all.

Instead, why not ask questions that shine light on your best qualities?….that you are well-read, funny, intelligent, well-spoken, kind, etc, etc, etc (there are just too many to list here).

Cheeky Questions to Put Your Best Foot Forward

Here’s my list of go-to cheeky questions to use on someone that I have just met, and I’d like to get to know better.

  • What character trait do you love the most in people?
  • Is there anything you can think of that you regret in your life so far?
  • When was the last time you peed your pants?
  • What is your funniest fear?
  • Who do you admire the most right now?

  • Do you have a nickname? If so, how did you get it?
  • Do you think this light makes us look good?
  • What part of the body do you appreciate the most?
  • Have you ever been skinny dipping?
  • Can you impersonate a celebrity (or do people ever say that you look like a particular celebrity)?

  • If you had a plane ticket to anywhere in your hand, where would you go?
  • What’s the best part of your regular average ho-hum day?
  • Name one thing you love about this city.
  • If you could go back to school, what would you study?
  • What cheers you up?

  • What habit are you proudest of breaking?
  • What is a skill that you wish you had?
  • What do you miss about being a kid?
  • Who out there is the world do you think knows you, 100%, through and through?
  • What’s your favorite kind of weather?
  • What is something you think is overrated but other people just love?
  • Name one movie you could watch again and again.
  • Is there a song that you could listen to on repeat?
  • What makes you happy?
  • Would you like to be famous, or rich?

  • Is cereal soup?
  • Is a hot dog a sandwich?
  • What’s the worst date you’ve ever been on?
  • What is the least attractive name you can think of?
  • When we are old, what do you think we’ll be nostalgic for?

  • What’s one thing everyone looks silly doing?
  • Have you ever been happy about burning a bridge?
  • What is best thing you’ve read in the past few months? (internet articles count)
  • What is the joke you like to tell the most?
  • Do you fold your pizza when you eat it?

  • Who was your favorite teacher and why?
  • Who would you like to live like for a day?
  • What’s your favorite time of day?
  • Who is the kindest person you know?
  • What is the worst thing you ever did as a kid?

  • What was the first person milking a cow trying to do?
  • Why do we say ‘after dark’ when we are talking about evening?
  • What’s the difference between normal ketchup and fancy ketchup?
  • What’s an ideal weekend look like for you?
  • Do you believe in second chances?
parents iphone
  • What is the first thing you notice about a person?
  • Is there something in your life that you are grateful for?
  • What absolutely excites you right now?
  • What is better….smarts or common sense?
  • Which of your parents are you closer to?
  • What is your favorite restaurant in the world?
  • What’s your biggest pet peeve?
  • What is the most significant difficulty you’ve ever overcome?
  • What’s one thing about the world that bothers you today?
  • Where do you see yourself in five years?
  • What’s the greatest risk you’ve ever taken?
  • What is your biggest irrational fear?
  • Have you ever seen something you can’t explain?
  • Where do you find your meaning in life?
  • How do you define art?
  • Would you rather love or be loved?
  • What’s the most adventurous thing you have ever done?
  • What trait do you envy in others?

Other things to consider

I don’t recommend holding a list like this and going down the list one by one. I’d definitely start with one question, and the follow up on the topics that come out of that answer naturally. I do recommend that you look at the other person’s face (and not your phone), especially at their eyes as they are talking. Don’t be afraid to check their body for clues about how they are feeling (open stance versus closed stance, loose hands and fingers versus tightly clenched hands or twitching and tapping fingers. This information can tell you a lot about your conversation partner, and whether or not you should stay on this topic or head down a different path.

If you think some of these questions are too wild or random, you can still ask them! You just need to preface the question with something like:

Hey, I want to try something different. Are you cool with that? I want to ask you some random, off the wall questions and see what you have to say! And you can ask me some odd-ball questions too. It’ll be a fun way to get to know you.

In most cases, so long as you don’t come out of left field with a completely random question, the guy will be down to chat about just about anything if he isn’t into you and the conversation.

Open Questions that invite more than one word answers

Try to get him talking. Some of the questions above invite short and to the point answers, but the majority of them are open ended, meaning that there is a lot your partner could potentially say in response.

You are the person asking the question should try hard to let him think about his answers, and then when he starts talking, try and let him complete the thought and what he has to say before jumping in with your own answer to the question, which might be burning you up.