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200+ Awkward Questions to Ask a Girlfriend and Knock Down All Walls

200+ Awkward Questions to Ask a Girlfriend and Knock Down All Walls

Updated on Nov 07, 2023

200+ Awkward Questions to Ask a Girlfriend and Knock Down All Walls

If you’re wondering why would anyone look for a list of awkward questions to ask a girlfriend, Well, it’s much better than throwing random pickup lines at your girl.

Whether you want to hit on someone or you found your dream boyfriend/girlfriend years ago, instead of trying hard and making accidental awkward conversations, asking awkward questions on purpose will keep things interesting for new lovers and fresh for old ones.

It also shows how smitten you are to blurt out in front of your girl… which makes her heart race!

So, don’t delay any longer and explore these…

Awkward Questions to Ask a Girlfriend over Text

Whether you both are “text people” or it’s because you communicate with her ONLY through texts due to the situation (long distance, huh?), use awkward questions to know her and her hidden feelings…

  1. Will you fall in love with me?
  2. Do you ever try to make your butt look big?
  3. Why were you single for so long?
  4. Do you regret knowing me?
  5. Do you think I might be in love with you?
  6. How many dudes did you date till now? How bad was the experience?
  7. How much must a man earn monthly to raise a family?
  8. Will you marry a broke man for love or an emotionally unavailable man for money?
  9. Would you like a slow dance and candlelight dinner date or an arcade and McD date?
  10. Why did you dump your ex?
  11. What is one thing you always expect from your partner on a date?
  12. Which Disney movie wedding are you most hooked on?
  13. Have you ever been on a blind date? What do you think about it?
  14. Who is your go-to love guru?
  15. Do you have enough money to pay for a date at *insert a fancy high-class restaurant name*?
  16. Are you still in touch with your ex?
  17. If your ex were to return, would you choose me or them?
  18. Did you ever fall in love with money?
  19. Do you feel jealous when I talk to other girls?
  20. How often do you lie?

So, she’s not just a crush but your girlfriend? My bad! Let’s find some basic funny awkward questions to also share a few laughs together…

Funny Awkward questions to ask a girlfriend

Naturally, everyone isn’t open to asking awkward questions because nobody wants to spoil their image in front of their girl. So, if you want to test drive this ride, let’s keep a hint of fun conversations with these…

  1. What one ice cream flavor are you ready to have for the rest of your life?
  2. Do you have an erogenous zone that isn’t usually sensitive to others?
  3. Did you ever have the hots for your boss or teacher?
  4. Did you ever give bad advice to anyone for revenge?
  5. Did you ever unintentionally scare away anyone with your sexual fantasies?
  6. Did you ever try phone sex?
  7. How grossed were you when you saw the male genitalia for the first time?
  8. If I cheated on you, which of my friends would you date for revenge? 
  9. Will you mind if we split the bill?
  10. Were you ever admitted to a mental hospital?
  11. Do you check my ass when I walk away?
  12. What’s your weight?
  13. Have you ever touched anyone’s butt accidentally?
  14. What’s your pet peeve?
  15. How will you react if I skip foreplay?
  16. What will you think if I made a seagull noise during sex?
  17. Did you ever wish you weren’t a girl? Why?
  18. Did you hate me before we started dating?
  19. How will you annoy me if you can be invisible for a day?
  20. Did anyone ever walk on you while changing?

If she responds well to these, know that she’s hooked. Now, you can add a hint of naughty questions (if you guys are in a long-term relationship and she’s open to sexual conversations) to steam up…

Sexual Awkward questions to ask a girlfriend

If you want to know your girl’s naughty preference in the bedroom and meanwhile also find out more about her life, these awkward yet brutally straightforward questions will help simmer intimate convo!

  1. Did you ever have sex while skinny dipping?
  2. Did you ever have a one-night stand while in a relationship?
  3. Have you ever role-played in the bedroom?
  4. Do you like to dominate or be dominated?
  5. Do you watch porn? What genre?
  6. How much erotica have you read till now?
  7. Did you ever work on your dirtiest sexual fantasy? How do you feel about it?
  8. Which scene from 50 shades of gray do you want to act out?
  9. What’s the sexiest outfit you own?
  10. What’s your biggest turn-on? How did you find out?
  11. Do you think technique or size matters?
  12. Which sex position are you too scared to try?
  13. What do you think of a quickie in the fitting room?
  14. Do you talk dirty in bed?
  15. If I apply peanut butter on my member, will you give me oral sex?
  16. How many sex toys do you own?
  17. Are you open to have sex with two men at once?
  18. Where do you want to be touched right now?
  19. Did you ever make a booty call?
  20. How long do you expect me to last in bed?

Is your relationship pretty new? Then the previous questions list might not be the best for your case. If asking awkward questions feels too random, that’s a great way to show off how spontaneous you are with these…

Awkward random questions to ask a girlfriend

Routine life and regularity are outdated and boring. Nowadays, girls hope their guys will bring spark and spontaneity to their life. Stun her with out-of-the-blue random questions and see her cutely fumble around for answers…

  1. If the Olympics had a tournament for anything and everything, what would you have a medal for?
  2. If you had the power to change the world, how many hours a day would mankind stay asleep?
  3. Did you ever want to be a stripper?
  4. Do you think sex is better in the morning or night?
  5. Did you ever drink and drive?
  6. What will make you never forgive me?
  7. Did you ever indirectly take a human life?
  8. Did you ever get stalked? What did you do about it?
  9. What would you never do to a friend?
  10. Would you get married to me if I asked?
  11. Did you ever use pepper spray on anyone? Who?
  12. Why don’t polar bears hunt penguins?
  13. Would you rather be a beauty without brains or a brain without beauty?
  14. Which of your habits did your exes hate?
  15. What’s that one career that you feel you’re unfit for?
  16. Which of your best friends do you think I might get jealous of?
  17. During a dinner date, your ex calls you incessantly. What will you do?
  18. On our anniversary, my close female friend gets hospitalized. What do you hope I’d do?
  19. If I sent you a picture of my privates and text “Wrong Chat”, how would you react?
  20. Would you ever consider creating an OnlyFans account with me?

But if your girl loves thought-provoking ideas, gets super immersed in intriguing themes, or if you think she’s a nerd, don’t waste your time and check these…

Awkward interesting questions to ask a girlfriend

If you both love to hold interesting conversations and lose yourself in the depth of your thoughts, there’s no better way to bond for you guys. Let your love bloom with these mind-boggling questions…

  1. If you had the chance to live in a game, what’s your choice?
  2. What’s your worst and favorite childhood memory?
  3. Are you willing to sacrifice your favorite food to save the world?
  4. If cell phones were banned, how many days until you die from boredom
  5. What is your favorite part of your body? What will you do if anything goes wrong with it?
  6. How long do you spend on social media aimlessly?
  7. What safety gadgets do you carry on the first date?
  8. How old were you when you signed in on social media?
  9. Would you rather live on a deserted island or live with zero privacy?
  10. How long must people take to get married from the onset of a relationship?
  11. Who are you closest to in your family?
  12. What unique family traditions do you wish didn’t exist?
  13. What’s the worst sexual activity according to you?
  14. What’s the best punishment for a cheater?
  15. What will you do if you see a couple having sex in the church?
  16. Which exam did you cheat on and how did you score?
  17. What’s your greatest regret about your career or academics?
  18. How much money would you never lend?
  19. Will you marry me for one night only?
  20. Did you ever force shut a sexual fantasy in your mind? What was it?

If you want to take it a level higher, you can totally ask her questions about her deepest beliefs, hopes, and desires. Now, that’s a great way to check your compatibility! So, jump in…

Awkward deep questions to ask a girlfriend

In relationships, compatibility in your beliefs and thoughts is an early marker of a strong and long-lasting relationship. So, if you’re curious whether you and your girl can stand by each other for all of eternity, ask these…

  1. Do you believe in marriage?
  2. If you want children but can’t have them biologically, what will you do?
  3. What do you want to change in society?
  4. How long is your oldest friendship?
  5. What is the longest your relationship lasts?
  6. How expensive of a wedding ring are you willing to buy?
  7. Do you ever think of your ex when we’re together?
  8. What do you think about pregnancy before marriage?
  9. Do you support white lies?
  10. Who is more important: me or your dad?
  11. Were you ever discriminated against? What did you do about it?
  12. For whose death will you cry the most?
  13. What’s the definition of cheating for you?
  14. What is the worst thing you expect from me?
  15. If you can change one of your body parts, what will it be?                                                                                       
  16. If your female best friend spends the night at my place, how will you feel?
  17. Did you ever have a parasocial relationship?
  18. Who is your role model or idol?
  19. When were you the happiest?
  20. How deep is your faith in God?

But if you know most answers to previous questions because you’re in a long-term relationship or know you have solid compatibility, congratulations! 

However, this means you must flirt a lot… c’mon, I’ll explain it all here…

Awkward flirty Qs to ask a girlfriend

In long-running relationships, flirting is a must to keep her excited and happy. Otherwise, despite the compatibility, she might get tired and bored of you. So, let’s strengthen your bond even more with a hint of awkwardness…

  1. Can I kiss you right now?
  2. Can you masturbate in front of me?
  3. In truth or dare questions, if someone dared you to masturbate publicly, what would you do?
  4. Did you ever make out in the cinema hall?
  5. How will you react if I talk dirty right now?
  6. What sexual activity is the most satisfying for you?
  7. During a zombie apocalypse, would you have sex with zombies if that stopped them from biting you?
  8. How old were you when you first got to know about sex?
  9. Rate yourself in the bedroom.
  10. What is the naughtiest thing on your bucket list?
  11. What did you think when you first masturbated?
  12. How many people do you think I’ve slept with?
  13. What’s the ideal frequency of love-making according to you?
  14. Do you like it with or without protection better?
  15. What color is your sexiest lingerie?
  16. Would you rather have me be aggressive or gentle in bed?
  17. If I were with you right now, what would you do to me?
  18. Where do you want me to touch you?
  19. How long do you think our love will last?
  20. Did you ever fantasize about me?

But, do you feel that you don’t know enough about your girlfriend? You wish to ask her some intruding questions but don’t know how… so, let’s help you frame your feelings here…

Awkward personal questions

Whether you want to know your girlfriend’s personal life before you met her or her deepest feelings about the relationship… if you want to get closer with small steps and deepen these bonds of fate, here you go…

  1. Who is a good kisser: me or your ex?
  2. Am I your type?
  3. At what age did you lose your virginity?
  4. What do you think is the best sex lingerie?
  5. Why did you want to date me?
  6. Which male friend do you secretly have a crush on?
  7. What do you think of sex at the workplace?
  8. Did any close one ever try to abuse you?
  9. Did you ever pee like a guy?
  10. Would you ever ditch a shopping date for me?
  11. Did you ever make out or kiss someone you mustn’t have?
  12. What do you think about going Dutch on the first date?
  13. Are you willing to share who you voted for in the last election?
  14. Do you strictly follow your religion?
  15. Have you ever shoplifted? Did you get caught?
  16. Is any of your family members an addict?
  17. Who was your worst heartbreak?
  18. Do you consider your parents’ relationship toxic?
  19. Do you sleep with clothes on or naked?
  20. What do you think about shower sex?

After intruding on her deep thoughts, “What if the ambiance might become too awkward to handle!” If that’s what you’re thinking, change her mood by making her cheeks flush with these questions…

Awkward and embarrassing questions to ask

If you love to see her act shy and look away with rosy cheeks and ears, shoot her embarrassing and awkward questions to know about her deepest secrets. Feel special while she shares her crude reality only with you…

  1. Have you ever lied about your age? What for?
  2. Did you ever moan another man’s name during sex?
  3. Did you ever get caught picking your nose?
  4. What is the worst pickup line you’ve ever used?
  5. What’s the worst thing your family members know about you?
  6. Did you ever embarrass yourself publicly and how?
  7. Did you ever walk into someone having sex?
  8. Did you ever overhear a conversation and get caught?
  9. When was the last time you peed in the shower?
  10. What’s the deepest secret of your life?
  11. Till what age did you wet the bed?
  12. How long did you go without brushing your teeth?
  13. Did you ever stalk anyone in real life?
  14. What age were you when you found storks don’t deliver babies in reality?
  15. Did you ever fart in an elevator and others couldn’t stand it?
  16. Would you rather walk naked down the street or have people read your mind for the rest of your life?
  17. Did you ever do anything that you considered cool back then, but now you’re embarrassed?
  18. Do you lick your fingers or your plate?
  19. What’s the worst reason you got grounded for?
  20. Did you ever piss in the pool?

On the other hand, if you just wanna be casual and showcase your normal weird side, that’s also an option! Get up close, intimate, and share awkward moments together here…

Awkward and weird questions

You probably thought you were a weirdo at some point in your life… but that’s just the sign of your unique heart. If you bear that part of you, she’ll definitely fall harder for you. So, let me show you how to do it…

  1. Will you ever have sex for money?
  2. Who do you see in your wet dreams?
  3. How long do you go without showering?
  4. How frequently do you fake orgasms?
  5. How many times do you wear your jeans without washing them?
  6. Did you ever catch any STI?
  7. Did you ever get addicted to drugs?
  8. Would you have sex with a girl [if she’s strictly heterosexual]/boy [if she’s strictly homosexual] for money?
  9. If my genitals get chopped off, will you still stay with me?
  10. Tell me one of your most embarrassing moments in life.
  11. What’s the worst thing you’ve got away with?
  12. Did you ever lick your mucus?
  13. Did you ever smear earwax on someone else’s clothes?
  14. Did you ever have a contagious disease, hid it, and socialized like normal?
  15. Have you ever farted loudly in a public restroom?
  16. What’s the worst text conversation you’ve ever had which isn’t about someone sending or asking you unwanted nudes?
  17. What useless product do you want to buy but know it’s not worth it?
  18. Will you ever pick up food from the ground and eat it?
  19. Which fictional character do you secretly want to date?
  20. Have you ever tasted period blood?

Wondering how awkward questions will help your relationship? Let’s reveal the secrets…

Why should you ask awkward questions to your girlfriend?

Most of you want to avoid being awkward to your girl at all costs and try to look cool and dashing.

But, girls always have a soft corner for the vulnerable shy guy that always has their feelings plastered all over their face. But there’s more to it, so know them all…

1. They are great icebreakers

You might fear that your girlfriend might be too stunned by your awkward question and not answer you at all.

But if you’re well-rehearsed and don’t blush after delivering the question, she’ll answer once she knows you’re serious and it’ll work like unconventional conventional starters.

2. It will help you share a laugh

Your awkward questions will shock your girlfriend about your audacity and even find it funny. Especially, if you look ultra-serious after delivering the question, she’ll be surprised, to say the least.

This will make her laugh at the moment and will give her something to reminisce about later on.

3. You won’t make a fool out of yourself

When your mind rages with millions of questions to sound cool to your partner, you’re prone to making a fool of yourself with some awkward questions.

However, if you deliberately ask awkward questions to a girl, you’ll seem confident and make a great impression on her.

4. You’ll stand out from the crowd

If you have yet to sweep her off her feet or if you’re not exclusive and lots of other people also court her, an awkward question is a strange way to stay on her mind longer and involuntarily make her think of you more. You’ll have a higher chance to score.

5. It’ll add spice to your relationship

In long-term relationships, people only use romantic, sweet, or sexy pickup lines to add spice. After a while, it gets boring.

But a hint of awkward questions can help you both explore deeper levels of your connection and bring the desired twist and fun to keep everything fresh.

A word from ThePleasantConversation

Awkward questions might help you hit things off in your relationship in an unbelievably great direction. You both will become extremely candid and close as you have more awkward and intense conversations.

However, if your girl isn’t ready to share something, don’t force her. If you allow her to keep some secrets, she’ll feel respected, loved, and cared for… and eventually, she’ll know you’re the one! When you earn her trust, she might even answer you later on.

So, just focus on what she tells you and not on what she refuses to tell you. And I’m pretty sure, you guys will have an amazing time… in love!