5656 Truth: What is your biggest regret?
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.
56. Truth: What is your biggest regret?
5555 Truth: What’s the most awkward moment you’ve ever had on a date?
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!
55. Truth: What’s the most awkward moment you’ve ev...
5454 Truth: What do you like about your crush?
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!
54. Truth: What do you like about your crush?
5353 Truth: What is your least favorite quality about yourself?
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.
53. Truth: What is your least favorite quality about yourself?
5252 Truth: Is it easy for you to say?
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.
52. Truth: Is it easy for you to say?
5151 Truth: What are you most afraid of?
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.
51. Truth: What are you most afraid of?
5050 Truth: Who are you jealous of?
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.
50. Truth: Who are you jealous of?
4949 Truth: What is your biggest turn-off?
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!
49. Truth: What is your biggest turn-off?
4848 Truth: What do you like least about me?
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!
48. Truth: What do you like least about me?
4747 Truth: What do you like most about me?
Why this is a good truth question: After the previous question, you are probably ready for a compliment!
47. Truth: What do you like most about me?
4646 Truth: Have you ever been rejected or rejected someone?
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!
46. Truth: Have you ever been rejected or rejected someone?
4545 Truth: What do you hide from your parents?
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.
45. Truth: What do you hide from your parents?
4444 Truth: What is your guilty pleasure TV show or music?
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.
44. Truth: What is your guilty pleasure TV show or music?
4343 Truth: Who was your first kiss?
Is the significance of a first kiss overblown in our culture? Maybe. Are all its details still fascinating? Yes.
43. Truth: Who was your first kiss?
4242 Truth: How old were you when you had your first kiss?
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.
42. Truth: How old were you when you had your first kiss?
4141 Truth: What do you wish you knew about girls?
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.
41. Truth: What do you wish you knew about girls?
4040 Truth: What do girls do that drives you nuts?
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?
40. Truth: What do girls do that drives you nuts?
3939 Truth: What do girls do that you love?
And on the other end of things, what do girls do that, with its feminine quality, drives him nuts in a good way?
39. Truth: What do girls do that you love?
3838 Truth: What pet names have you given your girlfriends? What have they given you?
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.”
38. Truth: What pet names have you given your girlfriends? What...
3737 Truth: What do you wish a girl would do to get in your good graces?
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!
37. Truth: What do you wish a girl would do to get in your good...
3636 Truth: What’s the worst thing about being a guy?
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?
36. Truth: What’s the worst thing about being a guy?
3535 Truth: What do you envy about women?
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?
35. Truth: What do you envy about women?
3434 Truth: What do you think would be the worst part 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.
34. Truth: What do you think would be the worst part about bein...
3333 Truth: What is the silliest thing you spend a lot of money on?
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.
33. Truth: What is the silliest thing you spend a lot of money ...
3232 Truth: What do you think girls look for in guys?
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.
32. Truth: What do you think girls look for in guys?
3131 Truth: Who do you think is an attractive man?
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.
31. Truth: Who do you think is an attractive man?
3030 Truth: If you had to go on a date with another guy, who would it be?
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!!!!).
30. Truth: If you had to go on a date with another guy, who wou...
2929 Truth: What mistake do you always make with girls?
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.
29. Truth: What mistake do you always make with girls?
2828 Truth: What’s the last thing that made you cry?
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.
28. Truth: What’s the last thing that made you cry?
2727 Dare: Text your crush that you like her
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.
27. Dare: Text your crush that you like her
2626 Dare: Use a cheesy pick up line on a stranger
Why this is 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!
26. Dare: Use a cheesy pick up line on a stranger
2525 Dare: Do the saltine challenge
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!
25. Dare: Do the saltine challenge
2424 Dare: Paint your nails
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!
24. Dare: Paint your nails
2323 Dare: Like a random girl’s oldest picture on Instagram
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.
23. Dare: Like a random girl’s oldest picture on Instagra...
2222 Dare: Go skinny-dipping
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.
22. Dare: Go skinny-dipping
2121 Dare: Crack an egg on your head
Why this is a good dare: This one is silly, but it is funny nevertheless!
21. Dare: Crack an egg on your head
2020 Dare: Walk around the block with your underwear over your pants
Why this is a good dare: He will probably get some funny looks that will embarrass him and make for good entertainment for you!
20. Dare: Walk around the block with your underwear over your p...
1919 Dare: Sing a song on the sidewalk
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!
19. Dare: Sing a song on the sidewalk
1818 Dare: Kiss me
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!
18. Dare: Kiss me
1717 Dare: Let us do your makeup.
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.
17. Dare: Let us do your makeup.
1616 Dare: Post your sappiest guilty pleasure song on a social media account.
We all have one, so get him to put his sensitive side on display. Post the most gut-wrenching lyric as the caption, too.
16. Dare: Post your sappiest guilty pleasure song on a social m...
1515 Dare: Sing us your favorite pop song.
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.
15. Dare: Sing us your favorite pop song.
1414 Dare: Do twenty push-ups.
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.
14. Dare: Do twenty push-ups.
1313 Dare: Let us wax your eyebrows
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.
13. Dare: Let us wax your eyebrows
1212 Dare: Send him to the drug store to buy a feminine product.
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.)
12. Dare: Send him to the drug store to buy a feminine product.
1111 Dare: Post a super weird selfie on social media.
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.
11. Dare: Post a super weird selfie on social media.
1010 Dare: Go borrow a weird ingredient from the neighbors.
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.
10. Dare: Go borrow a weird ingredient from the neighbors.
99 Dare: Eat a tablespoon of hot sauce.
The hard stuff. Perhaps that tablespoon of sriracha or Tabasco he just borrowed from your confused but accommodating neighbor.
9. Dare: Eat a tablespoon of hot sauce.
88 Dare: Let someone in the group send one text to anyone in his phone.
And then don’t give back his phone until the game is over. It will be AGONY.
8. Dare: Let someone in the group send one text to anyone in h...
77 Dare: Go have a conversation with a stranger.
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.
7. Dare: Go have a conversation with a stranger.
66 Dare: Have him act out a famous scene from a movie, playing every character himself.
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.
6. Dare: Have him act out a famous scene from a movie, playing...
55 Dare: Go serenade a stranger.
If talking to a stranger wasn’t hard enough, have him go pick up a lady of his choosing through song.
5. Dare: Go serenade a stranger.
44 Dare: Let someone give you a marker tattoo, then send a picture to your Mom.
Maybe your mom is cooler about tattoos than mine, but there’s a good chance his mom will flip.
4. Dare: Let someone give you a marker tattoo, then send a pic...
33 Dare: Do your best impression of me.
Or another person in the group of your choosing. This puts both of you on the spot, so if anything, it’s very fair.
3. Dare: Do your best impression of me.
22 Dare: Make up a fake identity and tell a stranger your story.
And the stakes get higher still! If he doesn’t come up with an accent and exciting backstory, he can do better.
2. Dare: Make up a fake identity and tell a stranger your stor...
11 Dare: Do your best impression of a female celebrity of our choosing.
Let the group come to a decision, then have him impersonate your chosen celeb for a set amount of time.
1. Dare: Do your best impression of a female celebrity of our ...