20 ‘Truth or Dare’ Questions to Ask Your Boyfriend

If you’ve ever played a round of Truth or Dare before, then you already know that it consists of asking someone a series of questions. If they decide to not answer them, they have to take whatever dare that you dish out. No matter how “daring” it might be.

The purpose of playing this game with your boyfriend is that it gives you the opportunity to get to know him a bit better. The key is not to ask really easy questions, but instead ones that will make him think long and hard about if he’d rather take the risk and go with the dare instead.

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Sound like fun? If so, here are the 20 questions that we think would make virtually any guy wonder if he should answer or do the dare.

1. “Have you ever cyber-stalked anyone?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“Have you ever cyber-stalked anyone?”/via

This is definitely one of our favorites. Not only does it reveal the vulnerability and insecurity of a guy but also if he has a darker (and jealous) side to him that he’s yet to show to you.

2. “What did you tell your mom about me?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What did you tell your mom about me?”/via

A lot of guys have a really great relationship with their mother. So, it’s always a good idea to know what he’s told her about you.

3. “What’s your grossest habit?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What’s your grossest habit?”/via

You would hate to find out on your wedding night that your man picks his nose (eww). Might as well get that all out in the open now, right?

4. “When did you first know you really liked me?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“When did you first know you really liked me?”/via

Everyone likes to know the time when their significant other realized they were the perfect one for them. Asking yours may provide you with a moment that you never would’ve expected.

5. “What’s your greatest physical insecurity?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What’s your greatest physical insecurity?”/via

By knowing about a guy’s physical insecurities, you get to discover a deeper side to him. Not only that but you can know which triggers to avoid. For instance, if he’s insecure about the size of his nose, then you can avoid making jokes about it.

6. “When’s the last time you lied?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“When’s the last time you lied?”/via

If all of us were really honest with ourselves, we’d admit that we’ve lied before. The key to this question is to find out how often your guy does it. And how far he’ll take a story once he starts.

7. “What’s your most embarrassing moment with a girl?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What’s your most embarrassing moment with a girl?”/via

A man who is willing to take about embarrassing moments is a guy who is willing to tell you almost anything. Hence, the recommend for this particular kind of question.

8. “What did you think about our first kiss?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What did you think about our first kiss?”/via

If you’ve been dating for a while, then you shouldn’t be scared to ask this question. Chances are, he felt butterflies because he’s still with you. And kissing you. It’s just something that’s nice and sweet to know. For the record.

9. “What’s the biggest lie you’ve ever told?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What’s the biggest lie you’ve ever told?”/via

There are “little white lies” and then there are huge “You did WHAT?!?” kind of lies. When it comes to your boyfriend, it’s a good idea to know about both.

10. “What really scares you?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What really scares you?”/via

This is simply something that’s wise to have on your radar. Some people have phobias that need to be shared.

11. “Do you still talk to your ex?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“Do you still talk to your ex?”/via

OK, this is the kind of question that you probably wouldn’t get an answer to unless you were playing this game. If he says “yes”, although you shouldn’t automatically assume that it’s a “bad” thing, at least you’ll be aware of the interaction. And that is a good thing. Especially if he tells you why.

12. “Would you post your fifth grade picture on social media?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“Would you post your fifth grade picture on social media?”/via

One way to get to know your boyfriend better is by hearing about his childhood. And seeing pictures of him during different phases and stages of his life. Posting it on Instagram is simply a way to make the dare so much more fun!

13. “What’s your guilty pleasure?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What’s your guilty pleasure?”/via

All of us have guilty pleasures when it comes to food, entertainment and so many other things. Basically, it’s getting to know someone on a deeper level. Without a lot of pressure.

14. “What are your three top insecurities?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What are your top three insecurities?”/via

Do you think that women are the only ones with insecurities? So. Not. True. Although it’s vulnerable for a man to share what his are, if you’re kind while he’s doing so, it will automatically make him feel closer to you.

15. “Would you passionately kiss me in front of your best friend?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“Would you passionately kiss me in front of your best friend?”

A man who is willing to embrace you in public, especially in front of one of his boys, is someone who is not shy about letting the world know that he’s into you. Awesome.

16. “What is your pet peeve when it comes to me?

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What is your pet peeve when it comes to me?”/via

It takes a pretty strong woman to be able to listen to what may get on her man’s nerves when it comes to her. But being open to hearing the information can also prevent a lot of drama/problems/confusion in the future.

17. “What do you think I’m more of: smart or funny?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What do you think I’m more of: smart or funny?”/via

Nothing super huge will come from this revelation. Other than knowing what your boyfriend finds more appealing: intelligence or humor. But of course, once you have that bit of info, you can then “turn up the notch, just a bit, on the one he likes the most.

18. “What’s your worst pick-up line? And did you use it on me?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What’s your worst pick-up line? And did you use it on me?”/via

Although pick-up lines have the reputation for better pretty corny and borderline ridiculous, you might be surprised at how subtle and charming some of them are. Especially if your boyfriend happened to use a few of them in order to get your attention.

19. “What did you tell your friends about me?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“What did you tell your friends about me?”/via

A lot of women would be floored (and perhaps even a bit embarrassed or even appalled) to know what men talk about. So, while you he might not tell you everything, if he does opt for “truth” on this one, at least you’ll have some idea of how he presents you to his friends.

20. “Do you see this lasting forever?”

20 'Truth or Dare' Questions to Ask Your Boyfriend
“Do you see this lasting forever?”/via

The only way to really know if you and he are on the same page is to ask. So…ask him.

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