100+ Awkward Questions to Ask a Girl


When you get an option to ask a girl any question or do something for you, what would you do? What if you had awkward questions to ask a girl?

We there is a game which precisely revolves around this logic called Truth or Date. Irrespective of any event, this game will bring twists and turns.

You want to learn all the deepest and darkest secrets of someone you like or just tease a buddy just for fun, or awkward questions to ask a girl, here is your opportunity to do so.

A simple yet fascinating game, which has no limits with complete reliability on the power of imagination. Creative imagination will certainly make this game much more fun.

There are only 3 rules here:

  1. A random person is chosen, the way to choose them is left to you
  2. Ask them Truth or Dare
  3. If they say Truth, you ask any question and they need to answer it truthfully. If they say dare, you need to provide them a task to complete and they are bound to finish it

See, no complicated rules. Keep it simple and fun which is not age restricted. Any age group can play this and on any occasion.

It’s always fun to learn new things about your friends and loved ones or make them do something fun or embarrassing. Unlimited fun for all as long as it is taken as a game.

Coming up with a unique question or a dare is not as easy as you think. Everyone will think about common questions to ask or common tasks.

However, if you have unique questions and dares, everyone will enjoy the game to the fullest.

Awkward Questions to Ask a Girl

Awkward questions to ask a girl or a guy are those that cause people to feel embarrassed or even uncomfortable.

To describe this better, the questions will be crazy, sex-related, very personal, inappropriate and weird.

Usually, couples play this game more than groups to find their level of intimacy. You may not want to step into the awkward part yet if the relationship is still in its early stages.

There are some questions which shouldn’t be asked at all, the conversation may end up in a relationship break up.

Some things are better left to be a secret than hurt yourself by knowing it.

An awkward question to ask a girl or a guy at the right time will bring more life to the game and the players. It can be made funny too which will make the players more comfortable to share secrets with each other.

An interesting answer to an awkward question will certainly lighten the mood in a date or even remove that embarrassing feel. This helps everyone participate more and with enthusiasm.

You need to ready to receive some strange looks when you ask these questions to a girl, to be honest, every girl will respond very differently to the same awkward question.

You need to be well prepared if things start to go south and try to salvage the situation.

Be broad-minded, there is no topic that is off limit these days.

However, you need to smart enough to judge what questions are suited to the current situation. Some negatives would be if the questions sound too out of bound.

As a personal note, I would like to point out that sex-related questions aren’t the only awkward ones. There are many mundane topics which will bring the awkward feeling to a person and there are a number of awkward questions to ask a girl or a guy.

I’ll also provide a few topics and questions related to it, which will help you understand the situation better before you pop the question.

Also Read: 50+ Extremely Hard Dares for Teenagers

Awkward Questions to Ask a Girl

  • How many guys have you been with?
  • What’s the wildest thing you have ever done?
  • Are you on your period?
  • Can we split the bill?
  • Have you ever done drugs?
  • What is ice-cream flavor disgusting?
  • What is the longest time you have stayed without having a shower?
  • Why are you single right now?
  • How much do you earn?
  • Have you ever faked it?
  • When did you lose your virginity?
  • Can I kiss you?
  • How long did your previous relationship last?
  • Did you escape from a mental facility?
  • Have you ever been arrested for doing or selling drugs?

Also Check: Truth or Dare Questions for Christmas Party Games

Inappropriate Questions to Ask a Girl

  • Has anyone ever accidentally seen you naked?
  • What is your darkest fantasy?
  • Do you check me out when I walk away?
  • How much do you weigh?
  • How old are you?
  • Is it that time of the month?
  • What clothes would you love to see a guy in?
  • What is your favorite part of a man’s body?
  • Which part of the man’s body should be tattooed?
  • When and whom did you lose your virginity to?
  • What’s your idea of a good foreplay?
  • Did you pick your nose without a tissue and when?
  • Have you accidentally touched the butt of another person?

Also Check: 150+ Questions for Valentine’s Day Party Games

Awkward Questions to Ask a Girl You like over Text

  • What’s the best thing that’s happened to you today?
  • What is your favorite place in the world?
  • Which is your favorite of the movie of all times?
  • What is your biggest goal in life right now?
  • What kind of music do you listen to?
  • Would you ever live in a foreign country?
  • What are you up to this weekend?
  • If you could choose to be an animal, which animal would you choose to be and why?
  • What did you do on your last vacation?
  • What three words best describe you?
  • What is your spirit animal?
  • Do you sing when you are alone, like in the shower or in the car?
  • What are you allergic to?
  • What do you do when you are bored?
  • Where is the most beautiful place you have ever been to?

Also Read: Truth or Dare Questions for New Year Party Games

Funny yet awkward Questions to Ask a Girl to Make Her Laugh

  • How would you describe yourself? Angel or devil?
  • What would you do if you were invisible for a day?
  • What is the weirdest nickname you ever had?
  • What is the weirdest crush you ever had?
  • What are the best and worst about being a woman?
  • What’s your favorite joke?
  • What’s the habit you hate most in a boyfriend?
  • What’s the worst thing someone has walked in on you while doing it?
  • If people could read your mind, what would they usually hear?
  • Would you rather be beautiful and dumb or ugly and clever?
  • If you could be a guy for one day, what would you do?
  • Who would you do between…?

Also Check: 100+ Dirty Questions to Ask a Girl

Relationship Questions to Ask Your Girlfriend

  • What was your first impression of me? Did you ever dislike me?
  • What’s your favorite memory of me?
  • What do you like best about me?
  • Who has been the most influential person in your life?
  • What’s your favorite color?
  • Who is your favorite actor? Actress?
  • How can I better support you in your life?
  • Is there anything that I might have done in the past unknowingly hurt you?
  • Do you need space or you want us to be closer?
  • Any argument that we had felt incomplete?
  • Is there any way I can reduce your stress?
  • Any speaking difficulties and how can I help at that time?

Also Read: 100+ Latest Dares for Boys and Girls

Interesting Questions to Ask Your Girlfriend

  • Who is your best friend?
  • What is your biggest fear?
  • What is the happiest memory from your childhood?
  • What is the one career that describes you or your lifestyle?
  • Where is the safest place in the world according to you?
  • What do you think is your best feature?
  • Are you a troublemaker?
  • Do you believe everything happens for a reason?
  • Have you ever had a near-death experience?
  • Have you ever been jealous of your closest friends?
  • Which habit are you proud of breaking?
  • If you go back in time once, what would you like to change your life and why?

Questions to Ask a Girl You Just Met

  • Would you like to be famous? In what way?
  • What is the one place in this world you wish you lived?
  • What is the coolest thing in this city no one knows about?
  • Do you dream often?
  • What’s the most romantic thing you have ever done?
  • What do you do in your free time?
  • Where were you born?
  • What’s your favorite restaurant?
  • Who is your go-to person to seek advice to resolve an issue?
  • Have you ever met anyone famous?

Also Check: 100+ Latest WhatsApp Smiley Dares

Questions to Ask Your Girlfriend

  • Describe your daily routine and the most enjoyable thing in that routine?
  • What do you think the role of women in a relationship should be?
  • Should roles change hen relationship grows and after marriage?
  • Have you ever cheated on someone? What happened?
  • Do you prefer being outdoors or indoors?
  • What objects are the most valuable to you? Name any three.
  • What if your best friend turns against you? How will you react?
  • What is your idea of a perfect weekend getaway?
  • What do you think is a waste of money?
  • What would 30 seconds you erase from your life?
  • What was the biggest teaching incident in your life?
  • What do you need to vent about?

Good Questions to Ask a Girl

  • Did a random stranger impact your life in any way? If yes, how?
  • What period in history had the best fashion?
  • Are you judgmental?
  • Which religion do you like the most and why?
  • What was your best and worst childhood memory?
  • Does any movie character describe you?
  • What startles you easily?
  • What’s the most immature thing that you have done?
  • What are you passionate about?
  • Where is the last place you would ever go?
  • Do you have any female role model? If yes, who is it?
  • What is the most unusual fear you have?

Best Questions to Ask a Girl

  • What are your secret skills?
  • What was your favorite childhood toy?
  • What was the best gift you have ever given someone?
  • What was your most embarrassing moment in school?
  • What would you grab first if the house is on fire?
  • What is your dream destination for a vacation?
  • What is the next thing to do on your buckets list?
  • What was your worst job?
  • Who gives you best advice? Is it a friend or family?
  • What sport were you good at growing up?
  • Would you go out with me?
  • What is the most common pick up lines guys use on you?
  • What is the meaning of your name?

Questions to Get to Know a Girl

  • Any past incident which made you grow into the person you are?
  • Which is your most comfortable place?
  • What is your escape strategy from outside world?
  • Do you think you have ever had a spiritual awakening?
  • What would you like to change about yourself?
  • Who knows your entire deepest darkest secrets in the entire world?
  • How would you like your relationship to progress? Slow and steady or love at first sight?
  • When and how was your first kiss?
  • Do you feel vulnerable? If yes, why and what makes you vulnerable?
  • What would be the first thing you would if you become an animal?

Final Thoughts

I did list all the possible good bad and ugly eggs here. I have tried to make a complete list of awkward questions to ask a girl. It is up to you to use them wisely.

Having said that, you are unique and you know yourself well enough to find out more about a girl who may or may not is in your life going forward.

Truth or dare came all the way to relationship goals and what to ask and what to avoid.

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