Skip to main content
Updated date:

50 Cute "Would You Rather" Questions for Your Boyfriend


I'm Tatiana and am a firm believer in the power of holistic healing and home remedies! Apple cider vinegar for the win!


"Would You Rather" is a fun game to play with someone and is an easy way to get to know them! It’s quite simple: You simply ask a bunch of questions that start with “would you rather” and give them two options. The person answering the questions must choose one of the options.

Some people will make alternate rules, such as if you refuse to answer a question, you must take a shot (if of drinking age), do a dare, or do something silly. If you’re getting to know someone, make it fun!

Getting to Know You

If you are seeing a new boy, then chances are you don’t know much about them, and you should play "Would You Rather!"

For your boyfriend, it can actually be fun for him too as he will also have the opportunity to get to know you through the same game!

When it comes to "Would You Rather" questions for your boyfriend, we have some of the cutest ones that will pick right into their personality and expose them!

So here they are...

Would You Rather...

  • Hold my hand or put your arm around my waist?
  • Kiss in public or kiss in private?
  • Go watch a movie or go watch the sunset?
  • Kiss on the cheek or kiss on the forehead?
  • Peck on the lips or French kiss?
  • Cuddle under the stars or cuddle under a blanket?
  • Slow dance to a romantic song or grind to a fast beat?
  • Ride bikes together or take a long walk?
  • Go to a photo booth or take silly selfies?
  • Me cook you breakfast in bed or a candlelit dinner?
  • Sing to me or play me a song on guitar? (Or whatever instrument he may play)
  • Dress up for a night on the town or go full casual?
  • Walk on the beach with toes in the sand or take a dip in the water?
  • Go skinny dipping or dive in fully-clothed?
  • Draw pictures in the sand or make pictures out of clouds?
  • Have a snowball fight or water balloon fight?
  • Go tubing or skiing?
  • Go surfing or jetskiing?
  • Take a shower with me or a bath with me?
  • Talk to me on the phone or through text messages?
  • Pass notes or send text messages?
  • Kiss on the first date or wait a few dates?
  • Watch a fireworks show or go watch a musical?
  • Go to a concert together or make music together?
  • See me with makeup on or without makeup on?
  • Get smacked on the butt or kissed on the cheek?
  • Go camping in the mountains or have a movie night in?
  • Go out for ice cream or make a sundae bar at home?
  • Go on a date with friends or just you and me?
  • Drink liquor at a party with me or drink wine over dinner?
  • See me in a bathing suit or in lingerie?
  • Me wear a thong or boy shorts?
  • Me wear your t-shirt or one of my skin-tight cami tops?
  • Ride a bike with me on the handlebars or a motorcycle with me on the back?
  • Dance under the moon or in a club?
  • Cuddle with me or make out?
  • Cook dinner with me or have me cook dinner?
  • Go out for fine dining or order some pizzas and soda?
  • Go on a road trip or fly to our destination?
  • Go on a destination cruise or take a flight?
  • Travel around the world or have a family?
  • Explore outer space or explore the depths of the oceans?
  • Buy a card or make a card?
  • Write a love letter or write a poem?
  • Receive a love letter or receive a poem?
  • Watch a romantic comedy with me or go shopping with me?
  • Get a tan at the beach or go to a tanning salon?
  • Get a pedicure with me or get a massage with me?
  • Send me to a spa or give me an amazing massage?
  • Receive a gift bought from the store or a gift made by hand?

Video: Romantic Gift Ideas for Boyfriends

Strategic Questions for Your Boyfriend

Not only is this game great for getting to know your new boyfriend, but it’s an easy way to drop subtle hints if you are ready to take your relationship to the next level, but are afraid to make the next move!

This can mean something as simple as you are ready to hold hands or even ready to pucker up for that first kiss (and that he better make it special)!

Otherwise, it’s a very innocent game and can be used to reveal any deal-breakers, too, so use it to your advantage!

You Might Also Like:

  • 25 Fun Things to Do With Your Boyfriend
    Looking for fun things to do with your boyfriend? Sometimes it’s difficult to come up with date ideas in a pinch so look no further! Here is a list of 25 fun things to do with your boyfriend!
  • 30 Dirty Would Your Rather Questions
    Whether you are on a first date or a party with close friends, these dirty Would You Rather can always create moments of laughter and moments of shock. It’s always a good time!

35 Cute Questions to Ask Your Boyfriend


Nikki on January 15, 2020:

Awesome article, amazing questions, loved it

Read More From Pairedlife

crissy on December 09, 2019:

Thank you for these questions now me and my boyfriend seem so much closer and he love these questions and he wont stop asking me for more.

Ryelynn on September 15, 2019:

Awesome questions I live them

katie-john on April 02, 2019:

i love him so much .

Emo Nemo on February 10, 2019:

me and my bf used these in a would u rather and were closer now thank you :)

Baeee on January 28, 2019:

My bf loves these questions...he wants more

❄️ on December 03, 2018:

He loves me and I love him

Hailey becerra on June 28, 2018:

This website got me and my bf closer, Love this website pls make more:)

YassssDaddddy on May 19, 2018:

Hai. My Boyfriend is addicted to these questions. Now he wont stop asking for more..HELP. SOS

bay on April 03, 2018:

me and my boyfriend loved the questions and also my friends to with there boyfriends

Rachel on March 28, 2018:

My boyfriend loves me even more after i asked him these questions!! Love It!!

Hate my LIFE on February 01, 2018:

not a good website he broke up with me for asking him these questions

i hate this website

lupita on January 31, 2018:

i like these would you rather questions

kitty on January 16, 2018:

this was ok wedsite

lol on December 22, 2017:

what is this is unbelive that they put these thing on wecsite like stp it no

You Know Who I Am on November 17, 2017:

So... I have a boyfriend now.... It's great.

BLEEP on September 17, 2017:

Not my type of questions.

NICHOLE on September 11, 2017:


POOOP on July 25, 2017:


alex on June 11, 2017:

we need more romantic ones like wyr kiss me or hug me

Esperanza on February 27, 2017:

We need sexier ones. these are cute but what if we want to know the sexy side of our Boyfriend?

Jess on November 17, 2016:

OMG i sent this to my boyfriend and he loves me even more!!

bri on November 11, 2015:

Omg! I asked my crush these and now we're dating!!

Sia from United Kingdom on February 24, 2015:

Love this article! Very useful :)

Related Articles