Best Funny Questions To Ask Your Boyfriend Over Text And He’ll Laugh His Head Off!

The biggest problem about texting is that it’s so casual and can end at any moment. But asking questions is the best way to keep the mood, right? Wait, I’m not talking about the common sports quiz questions or “whats your favourite food?” questions here. I’m talking about this HILARIOUS list that will keep you and your boyfriend stays on texting all day long!

Besides that, texting is an easy, fun, and enjoyable way to communicate with your boyfriend. In fact, even when you’re talking to a friend, family member, or significant other, texting is one of the best ways to get to know them better. You may want to read this post on how to send goodnight text to him because I have so many great tips for your relationship!

So, one of the best ways to strengthen the bond between you and your boyfriend is by learning how to ask funny questions and having a fun time together. If you’re looking for something really entertaining to talk to your boyfriend, you should try some of these fun and witty questions to ask him.

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Funny Questions To Ask Your Boyfriend Over Text – He’ll Fall For This One!

You can’t just leave it there. You need to keep your conversation going and be more creative. You can use the questions listed below to make him smile and laugh. Trust me, you’ll have a better time with a guy who laughs when you are being funny.

The best part is, these questions are also great for text messaging. You can message your boyfriend and ask him about these topics without feeling awkward. It’s a great icebreaker and he might even start sending some sweet messages back.

  1. What would you do if you were a girl for a day?
  2. What is the strangest item on your bucket list?
  3. What is one of your most humiliating stories?
  4. What is the most common misconception about you?
  5. What are some of your favorite pick-up lines?
  6. What are your favorite vices?
  7. Which portion of my body would you want to inspect first if you had X-ray glasses?
  8. What is the most unusual thing you’ve ever done for a girl?
  9. Who was the most recent person you attempted to impress?
  10. What’s the worst thing your parents have ever caught you doing, and how did you get away with it?
Funny Questions To Ask Your Boyfriend Over TextPin
Loshane | Source: CABANA CATALOGS Source: Unsplash

Important tip: If you want to be successful in your relationship, then try to tone down your wit while joking. While it’s okay to make some jokes and laugh when around your loved ones, it’s also important to avoid sarcasm because it could hurt your relationships.

  1. Are you kind or naughty?
  2. What was your strangest gift?
  3. Should your bank balance or internet search history be public?
  4. What will eventually break the internet?
  5. What’s your most humiliating crush-attracting move?
  6. Your favorite meal besides me?
  7. What’s your warning label?
  8. What was your most uncomfortable date?
  9. Which of these things do people believe make them appear cool, but really make them look ridiculous?
  10. Share the most embarrassing experience you had as a kid.
Best Funny Questions To Ask Your Boyfriend Over Text And He’ll Laugh His Head Off!Pin
Loshane | Source: CABANA CATALOGS Source: Unsplash

So, when asking your boyfriend funny questions, make sure to focus more on the fun stuff! It’s also a good idea to try asking open-ended questions so you don’t have to worry about the answer too much.

  1. What do you enjoy doing, but are too old for?
  2. Which fashion trend was your worst?
  3. When you get into the shower, what is the first thing you wash?
  4. Men have nipples—why?
  5. What’s the oddest thing you’ve done at someone else’s house?
  6. Which road rules are the stupidest?
  7. How long would you survive the Hunger Games?
  8. What’s your most embarrassing daily occurrence?
  9. Which awful film do you love?
  10. Your phone’s weirdest app?
Funny Questions To Ask Your Boyfriend Over TextPin
Loshane | Source: CABANA CATALOGS Source: Unsplash

To make your man laugh, tell him a joke, tell him a funny story, and be playful around him. This will give you the chance to know what type of jokes he likes to make. Once you know what kind of jokes that he likes, you can tell him more funny questions and jokes that relate to those topics.

  1. Tell me about the most unusual crush you’ve ever had.
  2. What song is playing while you prepare to kick some serious butt?
  3. What do people do that makes them look foolish?
  4. Which would you prefer: being able to just yell or whisper?
  5. What Hogwarts house does the Sorting Hat think you’ll be assigned to?
  6. Your wildest dare?
  7. What job should be created?
  8. Which fictitious friend group would you join?
  9. I say “sexy,” what comes to mind?
  10. What would be your superhero identity?
  11. What did you consider to be ridiculous before you actually attempted it?
  12. Which of the lies that you’ve told your parents is the most terrible one?
  13. What is it about you that makes me doubt something you’ve said or done?
  14. What’s the creepiest thing you might say to a stranger on the street?
  15. Which of the following would you want to do: dance naked by yourself or dance in front of a crowd?
  16. Your celebrity doppelgänger?
  17. Who would be your ideal spouse from the world of fiction, if you could marry anyone?
  18. What would you do if you had the ability to hide from everyone for a day?
  19. What would people call you if you were famous? What would be your stage name?
  20. What would you want your personalized license plate to say?
Funny Questions To Ask Your Boyfriend Over TextPin
Loshane | Source: CABANA CATALOGS Source: Unsplash

Emojis are such fun things, right?! They’re a quick way to convey meaning when written out in long sentences, but they also come in handy when writing a text. Using them in place of plain text is a great way to avoid sounding stilted, and a good way to catch the attention of readers.

  1. What is anything that is really popular right now that everyone will look back on and be embarrassed about in ten years?
  2. What’s the best WiFi name you’ve come across?
  3. Which podcast would you choose if your life were a podcast?
  4. Which mythical creature do you hope existed in reality?
  5. What would your signature move be if you were a wrestler?
  6. What is the most seductive vegetable?
  7. What is one ability you wish you had?
  8. What is the funniest dream you can remember having?
  9. Have you ever been caught naked in public?
  10. What was the first email address or screen name you used?
Funny Questions To Ask Your Boyfriend Over TextPin
Loshane | Source: CABANA CATALOGS Source: Unsplash

Best tip: Now, let’s talk about the main thing. Remember to keep the conversation fun and light-hearted. Don’t go into too much detail, or use serious language when it comes to expressing your humor. But yet, if you want to have some deep conversations, try these deep questions to ask your boyfriend!

  1. What high-level job could you lie your way without experience?
  2. Would you rather date someone who does stupid magic tricks the whole time or someone who wants to sell you beach body protein drinks at the end?
  3. Which foreign accent would you want?
  4. What would you eat dipped in chocolate?
  5. The worst “buy one, get one free” sale ever?
  6. Grocery cart scavengers—heroes or villains?
  7. What’s the best zombie takeover preparation?
  8. Play two truths and a lie? I’ll guess which two of your three statements are lies.
  9. Your worst embarrassing talent?
  10. What’s the funniest movie quote?
  11. What did you believe too long as a kid?
  12. Plan your ideal birthday. Where are we going, what cake are we eating, and what gift am I giving you?
  13. What do you wish we knew five years ago?
  14. Smart, humorous, or sexy?
  15. Your childhood nickname?
  16. What a random compliment stuck with you?
  17. What trend do you regret wearing?
  18. Your worst meal?
  19. Your hallmark dance move?
  20. What odd taste combination do you love?
Best Tip For Funny Questions To Ask Your Boyfriend Over Text Pin
Loshane | Source: CABANA CATALOGS Source: Unsplash

A quick tip, don’t double text! There are many guys who just want to keep it short and sweet. If he’s busy doing something else, chances are he won’t respond to you.

Wait for a few minutes and check his status if he hasn’t responded to your last message. Just don’t make it too obvious that you’re checking up on him. A subtle glance at your phone will suffice.

  1. Which pop icon would you be and why?
  2. Which kids’ movie scene haunted you?
  3. Skinny-dipped?
  4. Your most absurd reality?
  5. Your oddest trait?
  6. What always makes you cringe?
  7. What’s a popular meal you hate?
  8. What music makes you sing?
  9. Which societal norm annoys you?
  10. Have you been up to anything exciting today, except than talking to me, of course?
Funny Questions To Ask Your Boyfriend Over TextPin
Loshane | Source: CABANA CATALOGS Source: Unsplash

Think about this: You should always take care of your partner’s feelings first before making any moves. Don’t ask too many personal questions at once when you’re talking to your boyfriend. Also, don’t ask him questions that might make him feel uncomfortable at the early stage of your relationship.

  1. Which worthless topic do you know well?
  2. Who or what can lift your mood?
  3. Did you regret buying something outrageous?
  4. What song would you listen to forever?
  5. Your life’s theme song?
  6. Ketchup, ranch, or hot sauce—only one for life. Which?
  7. Which body part tickles you most?
  8. What law would you amend first as president?
  9. Your most bizarre dream?
  10. Which names are sexiest and least?

These were all the most common funny questions to ask your boyfriend over text. They may seem silly and weird, but they are actually totally fine! Go ahead, get that funny side out of your system, and have fun!

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