Good Truth or Dare Questions To Ask a Guy

Why this is a good truth question: Many people are embarrassed to talk about their biggest regret so he may end up choosing dare! However, if he is brave enough to divulge his biggest regret to you, you will get to know a more vulnerable side of him.

Why this is a good truth question: This is a great way to find out more about him/her and even who he/she used to date. This is a good icebreaker question as well!

Why this is a good truth question: It’s really fun to find out what qualities attract people to their crushes. If you have been wondering who he has a crush on, but don’t think he would be willing to answer that question, asking what he likes about her can be a great way to find some clues! Also, if he gets a little bit flustered, he may actually have a crush on you!

Why this is a good truth question: This is a great question to get to know him a little better. Even though you have your impressions about him, it will be interesting to hear how he would describe his major weakness.

Why this is a good truth question: Even if someone seems really fun and nice, their ability to apologize when they are wrong can be very revealing about their character. If the guy you are playing Truth or Dare with is someone you are interested in dating, you’re definitely going to want to know whether he is the kind of guy who is brave enough to say sorry instead of sacrificing other’s feelings to protect his pride.

Why this is a good truth question: Guys often like to act like they are tough and unbreakable, so finding out what he is afraid of will help you get to know a side of him that he may not have revealed before.

Why this is a good truth question: Even though jealousy is often considered to be a trait or feeling that is commonly associated with females, guys are jealous of things too. Finding out who he is jealous of will help you understand his insecurities and goals.

Why this is a good truth question: Even if you’re not interested in this guy as a potential romantic partner, people’s turn-offs and turn-ons are fascinating! On the other hand, if you do like him, this is a great question to ask if you want to see if you currently possess qualities that would make him unlikely to consider you as a potential future girlfriend!

Why this is a good truth question: The point of this game is to ask questions that aren’t normal everyday questions, so why not? Even if he says something that makes you feel defensive, remember that you asked the question so you need to be open to the answer!

Why this is a good truth question: After the previous question, you are probably ready for a compliment!

Why this is a good truth question: This can be a painful question for some people to answer, but rejection stories are a great way to bond!

He can take this one as deep as he wants, so you’re giving him the opportunity to open up without a ton of pressure. He can answer with something small and silly, or he can tell you something serious.

We all have them, so we really never judge when we hear that someone loves watching My Super Sweet Sixteen. All the same, it can certainly feel like a major admission.

Is the significance of a first kiss overblown in our culture? Maybe. Are all its details still fascinating? Yes.

This might be hard to answer if he was something of a late bloomer. A first kiss is a milestone, for everyone, and revealing the details feels very personal. It may make him feel more vulnerable than he’s used to.

Much is said of how women are such mysteries, but what is it, exactly, that guys don’t understand? This is a great question to ask if you’re crushing on him, because it’ll tell you how perceptive he is about women.

In the presence of women, he should choose his words carefully, but you asked for the truth: what is it that women do that totally grates on him?

And on the other end of things, what do girls do that, with its feminine quality, drives him nuts in a good way?

When you’re deep in a relationship, you and your partner exist in your own little world in which you may stop using each others’ names and start using a super weird nicknames and pet name that has become normal to you. Only in retrospect are these funny. Make him cop to having once answered to “cuddlebear.”

Men often want to be the one to make the first move, but not always. If a girl were pursuing him, what would he love her to do? If he’s honest, he might surprise you!

First of all, between us, yeah- guys have it better in our society. But being a dude has its setbacks, of course it does. What, in his opinion, is the biggest one?

Being a woman is hard, no doubt about that, but from a male perspective, some of it probably seems fun. What does he think would be great about being a woman?

And on the other hand, what does he think is the hardest thing? His answer to this question might be very interesting and tell you a lot about how he sees girls.

Talking about money might be our strongest and longest-standing social taboo. BREAK IT. But start small. You’re not asking for hard numbers or anything too personal, just his silliest spending habit.

He might be totally wrong, and that’s sort of the point. How guys perceive what girls look for is an interesting perspective and tells you a lot.

What, basically, does he think are good qualities in a guy, maybe even qualities women overlook? Men can be just as obsessed with being attractive to the opposite sex as women are, but they don’t do as much talking about it. So get him talking.

It’s just a question, but a lot of guys freak out when you ask this. It’s purely hypothetical (it’s just a date! You’re not even asking him to kiss the guy! Just dinner in a softly-lit restaurant, maybe share dessert…okay, maybe don’t get this specific unless you’re having fun torturing him), and if he refuses to answer or gets mad, that actually might be a red flag that tells you he’s insecure (or just plain NO FUN!!!!).

This one is pretty personal. It will tell you something about his character, his self-awareness, and also his attitudes toward women. If you’re after this guy, the information is useful to you, too.

You have to be brave and strong to answer OR ask this question. It might be something funny and relatable like, “One of those sad animal shelter commercials with the Sarah McLachlan song,” or it could be something serious, so be prepared for any answer.

Why this is good dare: He may resist this one, but if he chooses dare he has to do it! Texting your crush and confessing your feelings is scary for anyone, but at least he has you to keep him company while he waits for the response.

Why this is a good dare: Using a cheesy pick-up line is embarrassing and often leads to rejection, so hopefully he is a good sport and follows through on the dare because it will probably lead to a funny story!

Why this is a good dare: There are a lot of food challenges out there, but this one is especially funny to watch because most people are super confident they can complete it easily, and it usually ends up being quite a struggle. In order to complete the challenge, you need to eat six saltine crackers in the span of 60 seconds, without drinking any liquid. It’s a lot harder than it sounds, we promise!

Why this is a good dare: Most guys are freaked out by the idea of wearing “female” products, so it will be funny to put him out of his comfort zone!

Why this is a good dare: People “stalk” each other on social media all the time, but it’s something we do because we are confident that they won’t know. Having him like a random girl’s oldest picture is funny because it makes him look like a creep and he doesn’t know her well enough for it to be comfortable/easy for him to explain why he did it.

Why this is a good dare: It requires a lot of bravery to go skinny-dipping, but a dare is a dare! This is an awesome dare if you’re looking for exciting dares for your boyfriend.

Why this is a good dare: This one is silly, but it is funny nevertheless!

Why this is a good dare: He will probably get some funny looks that will embarrass him and make for good entertainment for you!

Why this is a good dare: Just like the last one, this dare will attract other people’s attention and embarrass him, which will be hilarious to watch!

Why this is a good dare: Obviously, only use this dare if you want him to kiss you. But if you’ve been dying for him to kiss you, now’s the perfect time to make it happen!

Truth or Dare has been around forever, but that doesn’t’ mean it’s ever going to get old! As you can see from this list, there are a lot of truth or dare questions to ask a guy so have fun with it! On that note, this game is supposed to be fun, so don’t choose any questions or dares that could cause emotional damage or physical harm!

If he lets this happen, he’s a good sport, so be nice. He doesn’t necessarily have to go anywhere, and you can just do his eyes and lips— no need to waste a ton of your good foundation.

We all have one, so get him to put his sensitive side on display. Post the most gut-wrenching lyric as the caption, too.

This is hard to do, but honestly, once he gets started on, “Shake It Off,” you’re going to start singing along anyway and it’ll be fun.

A lot of guys fancy themselves tough and athletic and oh-so-strong. This can be kind of annoying, because one, you don’t really care, and two, it might be all talk. Have him put his money where his mouth is, and no modified push-ups either! Make him do twenty for you, by the book.

Ok, use a light touch with this, because we all know the lasting humiliation of a bad eyebrow wax. Or you can wax a section of his leg. And if you have to go to the nearest drugstore for waxing strips because you haven’t got any on hand, all the better. Dare him go up to the register with the waxing kit, too! The great thing about this dare is that it’ll give him a taste of how tough girls really are and how much pain we can take.

This is not only a dare but a litmus test for how good of a boyfriend he would be. Will he run out to buy you tampons when you’re curled up on the couch in sweats and just realized you’re out? (He better.)

You can work out the details on the spot. Should it be a FIERCE selfie? An unflattering one? Him posing with a random object? He has to post it right then, without modifying his privacy settings, and leave it up.

I’m not talking about a cup of flour or sugar or an egg. Get him to knock on doors until someone agrees to hand over a can of Lima beans or a tablespoon of sriracha.

The hard stuff. Perhaps that tablespoon of sriracha or Tabasco he just borrowed from your confused but accommodating neighbor.

And then don’t give back his phone until the game is over. It will be AGONY.

This is good for when you’re at a big gathering or a public place. Exchanging a few words with someone doesn’t count. They have to have a legitimate, back-and-forth conversation for at least a few minutes.

Ideally, pick a scene that everyone in the group would recognize, with unique characters and iconic lines. He’ll have to dramatize all of them.

If talking to a stranger wasn’t hard enough, have him go pick up a lady of his choosing through song.

Maybe your mom is cooler about tattoos than mine, but there’s a good chance his mom will flip.

Or another person in the group of your choosing. This puts both of you on the spot, so if anything, it’s very fair.

And the stakes get higher still! If he doesn’t come up with an accent and exciting backstory, he can do better.

Let the group come to a decision, then have him impersonate your chosen celeb for a set amount of time.