70+ Awkward Questions To Ask A Guy | Teenage | BF | Friend | Dating 2024

This post will help you improve your conversational skills and finally let you feel completely relaxed around any guy.

Although every man is unique some guys will prefer some inquiries over others.

These awkward questions to ask a guy will assist you in finding exactly what you need in each case.

Awkward Questions To Ask A Teenage Guy

Awkward Questions To Ask A Teenage Guy

“When was the last time you cried?”

“Who is your least favourite friend?”

“How much do you weigh?”

“What was your most embarrassing moment?”

“What’s the weirdest thing you have seen while driving?” 

“What’s your most common first thought when you wake up?” 

“What are your exes like?”

Uncomfortable Questions To Ask A Boyfriend

Uncomfortable Questions To Ask A Boyfriend

“How many girls have you slept with?”

“Does this outfit make me look fat?”

“Who is your biggest celebrity crush?” 

“What was the weirdest habit you had as a child?” 

“Have you ever been attracted to another guy?”

“How much money do you make?”

“Have you ever cheated on someone?”

“Do you have a hidden tattoo?”

“How many girls’ numbers are on your phone?”

Questions You Should Never Ask A Guy

Questions You Should Never Ask A Guy

“What are you too old for but still enjoy?”

“Have you ever lied to your best friend?”

“Have you ever farted loudly in class?”

“What’s the weirdest thing you loved to eat as a child?” 

“What’s the worst thing you have done while drunk?”

“Are you insecure?”

“Have you tasted ear wax?”

“Have you ever been stood up on a date?” 

“Have you ever stuck gum under a desk?”

Blunt Questions To Ask A Guy

Blunt Questions To Ask A Guy

“Who among our friends do you think would be the best kisser?”

“Do you have a bad foot odour?”

“Have you ever been caught checking a girl out?”

“Have you ever practised kissing a mirror”

“Do you enjoy the smell of your fart?”

“Have you ever peed while sleeping?”

“Have you ever farted in an elevator?”

“How long have you gone without brushing your teeth?”

“Can you describe the smell of your armpits?”

“Have you ever tasted your booger?”

Awkward Questions To Ask A Guy About A Girl

Awkward Questions To Ask A Guy About A Girl

“How many girls’ numbers are in your phone?”

“Do you think teen girls are hot?”

“Why did you dump your last girlfriend?” 

Awkward Questions To Ask A Guy Friend

Awkward Questions To Ask A Guy Friend

“Have you ever walked into a wall?”

“What is the most embarrassing thing you did in a previous relationship?”

“What was your immediate thought when you first met me?”

“What’s the weirdest item you own?”

“What’s the worst lie you ever told your parents?”

“What’s your most abnormal guilty pleasure?”

“What do you think of yourself?”

“Have you ever vomited in a mall?” 

“Have you ever had a weird haircut?” 

“What’s the most awkward thing you ever wore?”

Awkward Questions To Ask A Guy Over Text

“What was the most embarrassing text you ever received?” 

“What do you think is the ugliest part of your body?”

“What part of your body would you replace with an improved digital version?”

Awkward Questions To Ask A Guy In Truth Or Dare

Awkward Questions To Ask A Guy In Truth Or Dare

“Have you ever tasted your sweat?”

“Do you have any silly nicknames?”

“What movie did you watch that made you cry?”

“Do you lick your plate?”

“Have you ever lied about your age? Why?” 

“What’s the weirdest job you have had?”

“What did you think was silly until you tried it?”

Awkward Questions To Ask A Guy You Like

Awkward Questions To Ask A Guy You Like

“Have you ever tried to pee while sitting down?”

“Do you have an STD?”

“Have you ever been arrested?”

“Do you ever admire yourself in the mirror?”

“How much money is in your bank account right now?”

“Are you looking to be in a relationship?”

“How often do you have girls visiting your place?”

“What do you wear when you sleep?”

“Do you dirty dance when you are all alone?” 

Awkward Questions To Ask A Guy You Are Dating

Awkward Questions To Ask A Guy You Are Dating

“What has been your most shameful experience?” 

“Have you had any addictions?” 

“Do you pee in the shower?”

“What was the last text you sent?” 

“Do you drool in your sleep?”

“What colour of underwear are you wearing right now?”

“What’s the worst thing you have done for love?” 

“Have you broken someone’s heart?”

“How often do you wash your underwear?”

Related Topics: