List of Fun and Awkward Questions to Ask Friends

Would you like to spend some quality time with your friends? You can easily make the interaction memorable. Read on to get a list of fun and awkward questions to ask friends.
| Tuesday, November 18, 2008

Friends play an important role in our lives. These special individuals not only help us in tough times but also know how to share the positivity and happiness that we encounter and experience from time to time. There are few things as enjoyable as catching up with a friend over a cup of coffee. To make the interaction even more enjoyable you can have a list of fun questions to ask your friends. This will allow you to know your friends better and help you to unravel the quirkier side of their personality. If you have this list of fun questions then you can ensure that your time will be spent in light hearted banter and you will walk away with a smile on your face. Here is the list of fun and awkward questions to ask friends:

  • Were you a part of the popular or elite crowd in your high school? Why or why not?
  • If you could go back and change something about your high school days what would it be?
  • Who did you have a crush on during high school? Did you express your feelings for that person?
  • Have you ever been fired from a job?
  • Have you had an erotic dream? What was it about?
  • What is your biggest regret?
  • Do you sing while having a bath?
  • How often have you driven over the speed limit?
  • If you came to know that someone in this room were gay then who do you suppose it would be?
  • Do you think it is okay to lie? When would it be alright?
  • If you think no one is looking what is the one thing you would do?
  • If you were gay who would want to have a passionate affair with?
  • If you were stuck on a deserted island which one book, movie and person would you want to take along?
  • When was the last time you indulged in binge drinking?
  • If you could marry a cartoon character who would it be? Why?
  • What did you most get into trouble for when you were younger?
  • Why do women shave their armpits and men don’t?
  • Which teacher did you feel attracted to when you were in school?
  • What is your most embarrassing moment?
  • What is the one thing that disgusts you?
  • What was your nickname in high school?
  • What was your first impression about me?
  • If you were to die tomorrow what are the things you would want to do before you die?
  • What was your favourite toy as a child?
  • Which movie title would best depict your life story? Why?
  • When you are alone what do you most enjoy doing?
  • Which is the one event that has had the biggest impact on you and your life?
  • If you are not doing anything what are you most likely to think about?
  • What do you love and hate the most about the human race?
  • Who was your first prom date?
  • If you were an alcoholic drink what would it be and why?
  • If you could be a car which one would it be and why?
  • Who is the first person that you think about when you get up in the morning?
  • When did you first travel by airplane and where?
  • Who was your first best friend? Are you still in touch with that person? If you parted ways why do you think that happened?
  • When was your first sleep over and where?
  • If you could be a politician who would it be? Why?
  • If you could be a religious or spiritual leader who would it be? Why?
  • What is the first thing you do when you get up every morning?
  • If you could spend a night with a celebrity who would it be? Why?
  • What was your first tattoo or piercing and where is it? What does it stand for?
  • Which one country would you want relocate to if you had the opportunity?
  • Who was the first person who broke your heart?
  • What does love mean to you?

Some other fun questions to ask your friends:

  • How come you get the pizza faster than an ambulance?
  • Why is it that they say penny for your thoughts and yet you have to put your two cents worth?
  • If feathers tickle people, do they tickle birds?
  • Do blind people see their dreams? And do colour blind folks see their dreams in black and white?
  • What does the term free gift mean? Aren’t all gifts supposed to be free?
  • If Barbie is the most popular then why do people rush to buy her friends as well?
  • If a turtle does not have his shell do you call him naked or homeless?
  • If Americans throw rice at weddings do Asians throw burgers?
  • If you have the speed of light and sound then can you find the speed of smell?
  • Did a clumsy javelin thrower discover the pole vault?
  • If sheep can’t sleep what do they count?
  • If a bedroom has no bed in it then what do you call it?
  • If while talking to God he sneezes then what do you say?
  • Does shaved ice have hair and is it shaved for people to call it shaved ice?
  • Where does a wandering mind go?
  • Why did the Dead Sea die? Who killed it?
  • If smoking is prohibited in gas stations then why are ciggarettes sold there?
  • Why can’t people tickle themselves?
  • If quicksand sucks people down slowly why is it called that?
  • Why do feet smell and the nose runs?
  • Why is the word abbreviated so long?
  • Why is clear regarded as a color?
  • If a building is already built why is it called a building?
  • Why is the term tourist season used when you cant shoot any?
  • Why is the lid of a coffin nailed down?
  • If doctors are so skilled then why is their work called practice?
  • Why does night fall and yet the day breaks?
  • If rain drops then why does snow fall?
  • Are crop circle caused by cereal killers?
  • Do you have crash courses for pilots?
  • How come it is alright to pick ears but not the nose?
  • How many weeks does a light year contain?
  • How much milk does a Milky way have?
  • If corn is used to make corn oil how do you make baby oil?
  • If peanut butter is used to make peanut butter cookies then what do you use to make girl scout cookies?
  • Why does Superman wear his shorts over the trousers?
  • Are ducks used to make duck tape?
  • If Microsoft is big then why isn’t it called Macrosoft?
  • Why is a pizza packed in a square box?
  • Why is the term "slept like a baby" used when babies wake up every few hours?
  • If doctors get to see you naked anyway then why do they leave the room while you change?
  • If a person with multiple personality disorder threatens suicide would that be considered as a hostage situation?

Here is a list of a few really awkward questions:

  • What color is your underwear?
  • If people point to their wrist while asking for the time then why don't they just point to their crotch while asking for the location of the bathroom?
  • Is your sister hot?
  • If you say you love me why don’t you marry me?
  • Do you think you are selfish?
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Reader's Comments

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Alexa on Monday, May 28, 2012
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I love these questions me and my sister were going back snd forth with them because we were bored.
Bubba on Thursday, December 29, 2011
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Most awkward questions but need more
Smart Speller on Saturday, February 5, 2011
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Its not duck tape silly its duct tape so tha question makes no sense :)
» Smarter Than Above replies to Smart speller on Sunday, March 27, 2011
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Duck/ duct tap was used in the army to waterproof ammo boxes hence the name duck tape, it received the name duct tape when people started using it on ducting (that one's more obvious)
Hillary Matthews on Friday, January 14, 2011
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These are some great questions. me and my friend asked each other these and we were on the phone going back and forth for like 2 hours!
Mel on Sunday, December 5, 2010
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Omg i love this site i hope u put more awkward questions lol there hilarious!! xd