50 Cute "Would You Rather" Questions for Your Boyfriend

Updated on February 5, 2017
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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 you give 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 questions, 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...

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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?

Would you rather...

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  • 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?

  • Receive a gift bought from the store or a gift made by hand?

  • 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?

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!

35 Cute Questions to Ask Your Boyfriend


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    • profile image

      kitty 5 days ago

      this was ok wedsite

    • profile image

      lol 4 weeks ago

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

    • profile image

      You Know Who I Am 2 months ago

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

    • profile image

      F***K**Y* 3 months ago

      I used this for a Would you rather game with my crush!

    • profile image

      BLEEP 4 months ago

      Not my type of questions.

    • profile image

      NICHOLE 4 months ago


    • profile image

      POOOP 5 months ago

      LOVE IT

    • profile image

      alex 7 months ago

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

    • profile image

      Esperanza 10 months ago

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

    • profile image

      Jess 14 months ago

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

    • profile image

      bri 2 years ago

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

    • Sia184 profile image

      Sia 2 years ago from United Kingdom

      Love this article! Very useful :)