Naughty Questions To Ask Your Boyfriend Over Text

They will also let you know if he's the type of person that would be fun to joke around with or if he is more serious. there are a lot of funny questions you can ask your boyfriend, but some are inappropriate so use this list wisely.

If you want to try asking these questions over text message, make sure you don't bombard him with questions, but rather send one or two at a time; otherwise, it can easily come across as an interrogation!

1. Have you ever had a wardrobe malfunction?

I know that if you ask your boyfriend about his wardrobe malfunctions, he'll tell you a story—and it'll probably be a good one.

Men are very visual creatures. They love to see girls in sexy outfits and they enjoy it when girls dress provocatively. And what do most men do when they want to see a girl in sexy outfits? 

They go shopping! So when you ask your boyfriend about his wardrobe malfunctions, he can't help but think of all the times he's seen girls in sexy outfits and how they made him feel.

If you're not sure what to wear, just keep this in mind: If it's something he would be attracted to, then it's probably something that will make him feel good. And don't forget that the clothes don't have to be too revealing—they just have to accentuate your best assets!

2. What's the weirdest thing you've ever done to get a girl to notice you?

Asking this question shows that you're thinking about things from his point of view as well as your own, which shows him that he should be thinking about things from your point of view too! 

This is a great way to get him thinking about how he could make things work with you instead of just ignoring what he thinks about you altogether.

Also, You may have heard of this thing called "the friend zone." It's where the guys you like end up putting you. It's a terrible place to be. It's not easy to convince a guy that you're amazing, but it can be done if you give him the right signals. 

If you're trying to get your guy to like you, asking him this is going to help start a conversation and show him that he should think about it.

3. Have you ever had a crush on someone that your friends didn't like?

This is an interesting question to ask. You may find out that he doesn't really have any friends or he is so popular that every girl he meets wants to be his friend. You could also find out that he has some really amazing friends, who have been with him through thick and thin. 

This will allow you to know how well he gets along with people he cares about. It's also a great way to see if he has any bad habits or addictions such as smoking or drinking.

4. Who are you jealous of and why?

 This question will help you understand your boyfriend's insecurities and the people who might be triggers for them so that you can be more empathetic and understanding if they ever come up.

A fight between you two could even start because of jealousy. If he is jealous of someone else, this gives him a chance to talk about his feelings for you and remind you just how much he loves you.

5. Have I ever caught your attention doing something weird?

Most people have things about themselves that are weird. Maybe it's the way their fingers wiggle when they're nervous, or the way they make a weird noise when they're eating cereal. If you ask this question, maybe your boyfriend will reveal his weirdest quirk to you!

6. Can you describe yourself in one word?

This is a fun question to ask him. It'll show you what he thinks about himself, whether he takes himself seriously, and how humble he is.

7. Who was your first kiss?

You should ask this kind of question to get a better idea of who your boyfriend is and what he values. For example, if you find out that his first kiss was with the mother of his best friend, you may learn that he values loyalty and family. Or if you find out that his first kiss was with the girl next door, you may learn that he values adventure.

8. Have you ever accidentally walked in on someone naked?

You should ask this question to make him feel comfortable around you.

There's no doubt that you're one of the best people he knows, but what if there are some things that you want to know about him—things that could be awkward if he weren't comfortable talking about them?

9. Do you want to tickle me?

Sometimes, it's hard to know if you should ask your partner a question. This is a question you SHOULD ask. It tells your partner that you're looking forward to seeing them and that you're comfortable with them.

10. Have you ever broken someone’s heart?

Because it is a naughty question that can be used to tease your partner. You will be able to find out what kind of attitude your partner has towards sensitive issues and how he deals with his past relationships. This can reveal a lot about his character. It can also allow you to see how much he values honesty in a relationship.

11. Have you ever been jealous of a friend or family member because of their success? What was that like for you?

This is such an important question to ask your boyfriend, not only because it opens up the topic of what his insecurities are and how he deals with them, but also because it helps you understand how he views the world. 

If he's never been jealous of anyone, that means he's likely a genuinely confident person with a good sense of self. But if he has been jealous, understanding why can help you understand what's most important to him, and how he deals with something that threatens those values. That can be really helpful when you find yourself needing to support him in a tough time.

12. What were some of the turning points in your life?

You might be surprised to learn that something you take for granted is actually a big deal for your boyfriend. Asking him about turning points in his life will give him an opportunity to open up and reveal something deeply personal, which can help you connect with him on a deeper level.

It's also interesting to ask what he thought of those turning points while they were happening because there are often things we don't realize until later on in life.

13. When did you realize you were all grown up?

This is a fun question that can allow you to reminisce with your boyfriend while also learning a bit more about him in the process. If he had a particularly tough childhood, there may be some dark moments; if so, it's possible that he dealt with those issues by moving on too quickly and not really taking time to grieve or heal.

If he had a great childhood, this could be an excellent opportunity for you to learn what made his life so good and how you might model those aspects in your own relationship.

14. What is something you did that you feel really guilty about doing?

You should ask this kind of question because you can find out how guilty your boyfriend feels about things and if it's a lot he might feel bad about some of the things he's done to you.

15. Is there anything that people do or say that gets on your nerves?

It is a good idea to ask your boyfriend questions like this because it will tell you if he is weak-minded and can't handle other people's behavior. If he can't handle other people's behavior then you will know not to hang around them.

16. What's your spy name, and what would you do if you were a spy?

Spy names are great because they're one of the few things that you can get to know about someone without asking them. It's not like you can just walk up to a guy on the street and ask him, "What's your spy name?" Plus, if you're in a new relationship and you want to know more about your boyfriend, asking questions is a great way to get him talking.

You might be surprised by what he comes up with! This is an interesting question because it will give you insight into his personality and how he sees himself in the world.

If his spy name is something like "Mr. Brown" or "007," then he's probably a pretty serious guy who takes himself seriously, too. He'll probably tell you all about his childhood fantasy of being a spy and what kind of gadgets he'd have.

17. What's your worst habit?

This is a great question to ask your boyfriend over text. Knowing each other's worst habits can help you find solutions that work for both of you. It can also help you know when to give your boyfriend space.

18. What's the biggest risk you've ever taken and what happened as a result of it?

This is a fun question that can lead to some hilarious answers. In this kind of situation, your boyfriend will either start telling you about how he jumped from a cliff that was really high, or he'll start talking about how he didn't have any money and had to walk home in the rain. Either way, you'll get an interesting story out of him!

19. What would be harder for you, to tell someone you love them or that you do not love them back?

20. When was the last time you cried in front of another person? 

21. Have you ever been arrested?

22. What toy did you use to play with as a child?

23. How neat and organized are you?

24. Would you rather be twice as smart or twice as happy?

25. What was the first thing that attracted me to you?

26. Have you ever wet the bed after the age of 8?

27. When did you realize you were all grown up?

28. What's your favorite movie and why?

29. What are you most thankful for in life?

30. If someone made a comedy about your life, what would the title be?

31. If you could pick three people, dead or alive to have dinner with, who would they be, and why would you pick them?

32. What makes you nervous?

33. What makes you cry?

34. What's your wildest fantasy?

35. Who do you get along with the best in your family?

36. Do you prefer a bath or a shower? How often do you take them?

37. What's your biggest turn-off — physical or personality-wise?

38. When was the last time you cried laughing so hard it hurt?

39. When was the last time you were really embarrassed by something that happened to you, and what happened?

40. What do people think is weird about you? Is it true?

41. What's your wildest fantasy?

42. Have you ever been caught while doing something naughty?

43. What's the meanest thing you've ever done to someone?

44. Who do you think is the hottest person in Hollywood?

45. When did you first realize that you were attracted to me?

46. What do you hate about me the most?

47. What's the farthest you've gone on a first date?

In conclusion, there are numerous questions to ask your boyfriend before you accept him and even more when you are completely in love and want to know some deep things about each other.

Now you know 47 questions to ask your boyfriend over text that he really wants you to know and I hope that some of them will encourage you to have a rock-solid relationship with your boyfriend.