47 Awkward & Embarrassing Questions to Ask a Guy You Like

From funny awkward questions to weird conversation starters, we've got you covered. We've also got some tips on what to avoid.

Updated January 15, 2024
guy and girl laughing

A little bit of awkwardness can somehow be bonding, especially when you're sharing embarrassing moments or those deep secrets you've never told anyone. There are some embarrassing questions to ask a guy that can help him open up (or just laugh), and there are others you should try to avoid if you want him to feel comfortable with you (especially early on).

Deeply emotional or intimately probing questions can be embarrassing for both of you if you're not at the right relationship stage to discuss them, but there are some uncomfortable questions to ask a guy that can actually help bring you closer. It's all about timing.

Embarrassing but Funny Questions to Ask a Guy

Some questions are embarrassing for you to ask and some questions are embarrassing for the guy to answer. These may make him (or you) a little uncomfortable, but they'll also make you both laugh.

  • Have you ever been caught doing something and had to make up a story to explain it?
  • Can I give you a makeover?
  • What's the strangest thing you've ever worn?
  • What's the most disgusting thing you've ever eaten?
  • Would you rather have someone walk in on you while you were in the bathroom or catch you picking your nose?
  • Have you ever had a wardrobe malfunction when you were in a public place?
  • Have you ever wet your pants?
  • What's the most embarrassing thing that's ever happened to you?
  • When have you completely misunderstood something and ended up looking silly?
  • Have you ever made a mistake that ended up being hilarious?
  • Have you ever practiced kissing on your own arm?
  • How many of the numbers in your phone are for people who have seen you naked?
  • What food are you really bad at cooking?
  • What's the strangest thing that's happened in your romantic history?
  • Is there anything you've worn (like a fashion trend) that you wish you hadn't now?
  • Have you ever used a word wrong and realized it later?
  • What's the strangest place you've ever gone to the bathroom?
  • What strange habit do you have that no one knows about?
  • How long does it take you to get ready for a date?
Quick Tip

Read his signals to see how much you're embarrassing him. The more you press someone for an answer, particularly one they may not want to give, the more likely you are to embarrass one or both of you. Stop if you feel like it's getting to be too much.

Related: 100+ Fun Relationship Questions 

Weird Conversation Starters That Work

Sometimes weird and potentially embarrassing questions can work as fun conversation starters. Although they can sound slightly embarrassing coming out of your mouth, these questions can lighten the mood. Look for funky topics that will get him talking.

guy and girl talking
  • If you held a world record, what would it likely be for?
  • If you could be any insect, what would you be?
  • What location in the world are you least likely to visit?
  • What's the one app you couldn't live without?
  • How long could you survive without your phone?
  • If you could be inside any game, which would you pick?
  • In an ideal world, how many hours a day would you be awake?
  • If you could go back to school for one year, which grade would you choose?

Related: 150 Hilarious Would You Rather Questions for Couples

Embarrassing Questions to Get to Know Him Better

Some of the most embarrassing questions are those that push the envelope of taste and decorum but still get at an important topic. These questions aren't always easy to ask or answer, but they're important conversations to have (especially if you're thinking about getting serious):

  • When was the last time you cried?
  • How much debt do you have?
  • Have you ever killed or seriously injured anyone?
  • Have you ever been arrested?
  • Would you ever watch pornography?
  • Do you love me?
  • Do you think you can fall in love with me?
  • Why did you break up with your last partner?
  • How many people have you slept with (or kissed)?
  • Do you ever want to get married?
  • Do you ever want to have children?
  • Do you have any STDs?

Related: 60 Questions That Help You Get to Know Someone 

Potentially Embarrassing First Date Questions Not to Ask

First dates and blind dates are awkward enough without adding unwanted tension from badly worded questions. If you want to make it to the second date, avoid these embarrassing questions and stick with safer topics.

  • Does this make my butt look big?
  • Do you have enough money to pay for the date?
  • How much money is in your bank account right now?
  • Why are you dating me?
  • Do you think about your ex while you're with me?
  • If you could change one thing about my body, what would it be?
  • Can you guess how old I am?
  • How much do you think I weigh?
Quick Tip

Even if you're not on the first date, it can be too soon to ask certain questions. Asking him probing or embarrassing questions before your relationship is ready for it can feel invasive and even disrespectful. Your relationship goes through different stages based on your individual emotional baggage and chemistry, so take it slow unless you know what's the right pace for the two of you.

Related: 21 Foolproof Things to Talk About on the First Date

Timing Matters With Awkward Questions

It's totally normal to be curious, and a great conversation can help you know each other better. Many of these questions are curiosities that may or may not come up during natural conversation. The key to keeping your interaction from being a bad kind of embarrassing is the right timing. No matter what kind of awkward questions you ask a guy, you're all set as long as you read his signals and consider his feelings.

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47 Awkward & Embarrassing Questions to Ask a Guy You Like