How to Play Truth or Dare with a Boyfriend

Co-authored by Laura Bilotta and Amy Bobinger

Last Updated: March 23, 2023 References

Truth or Dare can be a fun way to ask your boyfriend things you really want to know—or dare him to do something you really want him to do! We'll help you come up with cute, flirty questions and dares so you can get started.

Method 1

Method 1 of 2:

Thinking of Questions

1
Don't ask questions you don't really want to know the answer to. Truth or dare is meant to be a lighthearted game to bring you and your boyfriend closer together, but if you pry too much, you could end up hurting the relationship. Think carefully about the questions you choose, and don’t ask anything you’d really rather not know.^{[1]
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- Don't try to uncover deep, hurtful secrets, and beware of asking too many questions about his previous relationships. You could end up with hurt feelings, or you could dig up painful memories he'd rather forget about.
2
Use the game to find out anything you've been too shy to ask. Maybe there’s something you’ve always been curious about, but it never seemed like the right time to bring it up. Truth or Dare is the perfect excuse to get the answer to whatever’s been nagging at you!^{[2]
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- If you’ve always wanted to know why he has a tattoo of a lion on his shoulder or why his nickname is “Turbinado,” now’s the time to ask!
- Other questions might include something like, “What did you think of me when we first met?” or “Did you know that I liked you before we ever started talking?”
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3
Learn more about him by asking about childhood memories. Sometimes guys can be a little reluctant to talk about themselves as a kid, thinking it might make them seem less “manly.” Show him that you care about all of the experiences that shaped him into who he is by asking questions about his childhood!
- You could ask something like, “What’s your favorite childhood memory?”
- Get even more specific by asking, “What was the best birthday you ever had?” or “What was your favorite toy when you were little?”
4
Ask him about his hopes and dreams to get him to open up to you. Talking about the future doesn’t always have to mean planning your relationship together. If you’ve ever wondered how he pictures himself in 5, 10, or 20 years, ask him!^{[3]
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- For instance, you might say something like, “If you could have any job in the whole world, what would it be?”
- You could also ask, “Where are 4 places you want to travel to some day?”
5
Get flirty by asking him what he likes best about you. Give him the chance to compliment you by asking him what he sees in you! You can ask him specifically what qualities he likes, or what physical features he loves, or you could leave it open-ended.^{[4]
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- For example, you could say, “What’s something you love about me?” His answer might be your eyes, your style, or the way you always answer the phone when your little sister calls, no matter what.
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Find out what he thinks of himself with your questions. You can get a lot of insight into someone by asking questions about how they see themselves. Just like asking him what he likes about you, this line of questioning can either be specific or can leave him room to interpret it however he wants.^{[5]
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- You could ask him something like, “What’s your favorite part about your face?” or “What’s your least favorite body part?” to learn how he sees himself physically.
- To get to know his values better, ask him, “What’s the moment in your life you’re most proud of so far?” or “What’s something you really regret doing?”
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Ask him what he would do if he woke up and he was a girl to get silly. Not all of the questions have to be serious! Mix in some silly questions, like what would happen if he suddenly discovered he was a female.^{[6]
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- Other silly questions might include, “What animal would you be if you had to pick one?” or “What celebrity would you trade bodies with?”
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Challenge him by asking things he might not want to admit. As the game goes on, you should pick harder and harder questions for him. While you might not want to ask him anything too secret, you can find out things he might not admit otherwise!
- Ask him questions like, "What's your biggest fear?" to find out what he's afraid of.
- You could also ask him something like, "What's the most embarrassing thing that's ever happened to you?" or "What's your grossest habit?"

Method 2

Method 2 of 2:

Getting Creative with Dares

1
Don't dare him to do anything that might get him in trouble. Truth or Dare is a fun game, but it can get out of hand if you’re not careful. Avoid any dares that might make someone else mad, break any laws, or damage any property.
- Also, don't force him to do anything he doesn't want to do. It's okay for Truth or Dare to push a person out of their comfort zone, but it shouldn't leave them feeling uncomfortable.
- Keep it light. You should focus on fun and playful dares rather than embarrassing or risky ones. You can dare your partner to do something silly or make a funny face instead of asking them to reveal their deepest secrets.
2
Get him to take a selfie wearing something of yours for a fun icebreaker. If your boyfriend picks dare, tell him he has to pick one item of yours and take a selfie wearing it. Tell him he can pick an item of your clothing, makeup, nail polish, or accessories, but it has to be visible in the picture.
- If you’re playing at your house, tell him he can pick from anything in your closet or makeup table.
- If you’re playing somewhere else, gather some makeup and accessories from your purse and what you’re wearing and let him choose.
- To up the stakes, tell him he has to post the picture to social media and leave it there for at least the rest of the game!
3
Have him make a prank call to a random number for a classic dare. Prank phone calls are one of the most universal dares in Truth or Dare, but it's a little harder to make an anonymous call now that almost everyone has caller ID. To avoid this, have your boyfriend dial *67, which will block his number, then call a random number and try to keep the conversation going for as long as possible, or tell him he has to use a silly voice and that he’s not allowed to laugh until the person hangs up.^{[7]
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- Don't do this if it's really late at night, or the person he calls could get really upset.
4
Challenge him to pretend to be an animal for 5 minutes for a silly dare. You can pick the animal, or you can let him choose, it’s up to you. Set a timer, then have a laugh as he crawls around, pretends to eat, or whatever else his animal does.^{[8]
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- Some silly animals to choose from include monkeys, birds, snakes, or fish.
- Make this dare a little more flirtatious by telling him he has to be your puppy for the whole 5 minutes. Pet him and try to teach him to do tricks!
- You could also dare him to pretend to be a robot instead of an animal.
5
Make him talk to the wall as if it were you to see what he really thinks. If you want to find out what he wishes he could say to you, tell him that he has to pretend the wall is you and talk to it for the length of time you choose. He might flirt with the wall, tell it how much he loves it, or get something off his chest that he’s been wanting to say for awhile!
- Keep in mind that he might think it’s funny to tease you by saying things to the wall that he doesn’t mean! Try to keep a good spirit about it, and get revenge during your next dare if you need to.
6
Tell him he has to go outside and sing loudly to amp up the game. As long as you won’t be disturbing anyone who’s trying to sleep, this dare shouldn’t get you into too much trouble, and it will take your dares up to the next level. Pick a song with simple words, or one that your boyfriend knows well, and tell him he has to go outside and sing it at the top of his lungs.
- To make this dare more embarrassing, pick a nursery rhyme!
- Other dares involving singing could be to lip-synch to a pop song by a female artist, acting out all the moves, or having him sing in a high-pitched, cartoon voice for a whole song.
7
Make him do 20 push-ups to give him a chance to show off. Guys love having an opportunity to show how strong they are. If your boyfriend is athletic or works out a lot, dare him to do 20 push-ups, then sit back and enjoy watching him break a sweat!^{[9]
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- Just be ready, because he might dare you to do the same thing!
- Other athletic dares could include army-crawling across the room, sprinting around the block, or standing on one foot for as long as he can.
8
Get him to dance for a silly challenge. Dancing is always a fun dare, and it should have both of you laughing in no time. The dare might be that he has to dance in a certain way, or for a certain time, or whatever else you can think of!
- For instance, you might dare him to dance without any music for 60 seconds.
- You could also pick a song and tell him he has to dance to it from beginning to end, or tell him that he has to break dance or try to do the worm.
9
Tell him he has to make a face mask out of ingredients from your fridge. Let your boyfriend create his own spa treatment from whatever you have on hand. Tell him he has to leave the mask on for 3 minutes, but that you'll help him wash it off after the dare is over.
- Some funny ingredients to use could include ketchup, peanut butter, cheese slices, and pickles.
- Avoid anything spicy like hot sauce or mustard, as well as anything acidic like lemon juice, since these can cause an adverse skin reaction.
- To wash off the mask, dip a wash cloth in warm water and gently wipe his face clean. Be sure to tell him how great his skin looks!
10
Dare him to kiss you near the end of the game. This is the ultimate Truth or Dare challenge, and he’ll probably be expecting it all along. Make him wait for it, so the game doesn’t just turn into a make-out session. Depending on what you’re comfortable with, the kiss can be closed-mouth or deeper, but make sure you know ahead of time what you’re willing to do.^{[10]
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- For a fun twist on a classic dare, dare him not to kiss you instead. Then, get your lips as close to his as you can to see if he’ll play by the rules!

Community Q&A

Question

What if I don't have a boyfriend, can this work with a crush or just a friend?

Community Answer

It depends on the questions, but I say go for it! It really shouldn't make that big of a difference.