20 Cute Questions to Ask Your Boyfriend

cute questions to ask your boyfriend


Cute and Interesting Questions to Ask a Guy You Love

When you think about cute things to ask your boyfriend one of the first things that comes to mind is childhood! These super cute questions are a great conversation starter for you and your man, and it also gives you the opportunity to find out what his childhood was like and just how ornery he was or still is. These questions should bring out some embarrassing answers you can use against your boyfriend in a playful manner later on. I love finding out things about my boyfriend’s childhood. It’s strange to think, thinking about him as a little kid would make me fall more in love with him, but it did. If you can coax some old pictures out of him too, it’s quite fun.

1Who was your first celebrity crush?

We all have one. It might have been the main character of his sisters favorite TV show, or it might have been a news anchor. Whatever the case this is bound to be good. Maybe it was even Vanna White from Wheel of Fortune.

2Did you have a “girlfriend” in elementary?

Again, I think we all had the fake “boyfriend” or “girlfriend” in kindergarten. Maybe it was the girl down the street, or the girl who rode the bus with him. This little kindergarten cutie may have even been his first kiss! Awe, what a cute story.

3Did you ever try to pull any pranks on your parents when you were little?

I distinctly remember standing on the back of the couch close to the kitchen door and hollering for my dad. When he came through the door I threw a blanket over his head and laughed and laughed. It was pretty dang funny when I was 6 and now… well it still is pretty funny. Since boys seem to make more trouble, you man probably has some great stories.

4Are you still friends with anyone from elementary or junior high?

This one is a little more serious. There is a saying out there that if you are friends with someone for more than seven years, the bond will last a lifetime. There’s a good chance if your man is still friends with someone from his childhood, that they have been friends for more than seven years. It’s important to know who are important people in his life.

5Did you have any childhood pets?

Some kids aren’t allowed to have pets while some kids have five dogs, two cats, and a goldfish. Usually pets and kids share a sweet bond and hearing about how much your man loved Lucky his golden retriever will be a very sweet story. When I asked my boyfriend about his pets growing up, he said all of his dogs always had a blue collar. We just got a puppy and guess what color collar I picked out for him!

6Did you ever think about running away?

Or did you ever run away. How close did he get to actually packing his bag. And why in the world would you want to run away?! And last, just how far down the street did he make it. Typically, kids reasons for wanting to run away can be pretty funny, but also prepare yourself for maybe a more sensitive reason. Sometimes kids want to run away when their parents are fighting.

7Were you a trouble maker or a good kid?

If he was a good kid this might not be a very exciting question; however, if he was a troublemaker there might be a very interesting strand of stories coming.

8Do your parents have an embarrassing story about you they always tell?

All parents do. I had a kitty when I was little and my parents were taking it to get its claws taken out so it couldn’t scratch me anymore. I started crying because I didn’t want them to take my kitty to the doctor, but then at the last minute I asked if they could take it’s teeth out too. My parents laughed and laughed. Little kids are just great.

9Did you ever do something that your parents still don’t know about?

You broke your moms favorite lamp and blamed it on the dog. You lost your dad’s favorite tool and blamed it on the neighbor. Bounced your little sister off the trampoline and into the bushes. This list could go on and on.

10Who was your hero when you were a kid?

I think we’ve all seen pictures on the internet of a little kid crying because he got to meet the garbage man or smiling ear to ear standing next to a firemen. Little kids see the good in everyone and sometimes think really lame things are awesome. Maybe your man’s hero was a Power Ranger or maybe it was the guy who changed his parents oil in their cars, you never know!

11What’s the most embarrassing Halloween costume you wore when you were a kid?

I dressed up as a Teletubby… point made. There was a picture on the internet a few months ago of a little kid dressed up as a fart. Kid’s just don’t care how ridiculous they look.

12Were you a Momma’s boy?

If he loves his momma, he knows how to treat a girl with respect. But this could make for a funny story too. Did he put on his mom’s heels and walk around the house?

13Who was your idol in junior high?

The king of all embarrassments. Our junior high years are the ones we wish to forget over and over again. We walked talked and dressed like our idols. Luckily, my parents like to watch reruns of Friends and mine was Jennifer Aniston. I didn’t fall into the thick eyeliner, Avril Lavigne stage.

14Did you play peewee sports?

And does your mom have old videos!? Little kids playing sports is hilarious to watch. Did he play soccer, football, t-ball, or did his mom sign him up for gymnastics. Be sure to keep this locked away in the vault for when you hang out with his parents some time.

15What did you want to be when you grew up?

Astronaut, ninja, cowboy, accountant. You never know what little kids have running through their heads. At one point I thought I wanted to be an astronaut teacher because I thought by the time I grew up there would be people living on the moon. Obviously my dream was to much for our parents generation and our generation to handle. Maybe our kids will live on the moon.

16Did you wear something ridiculous like a superhero costume for days?

This seems to be a trend for many little boys, and a great trend if you ask me. Dressing up in princess dresses and plastic high heels was my life as small child. I can only imagine how fun it is for little boys to run around the house in a spiderman costume shooting imaginary webs out of their hands.

17Did you have a crush on a teacher?

Let me tell you now, he did. Don’t let him lie. Every little boy gets a crush on a teacher or a teacher aid at some point in their life. Get the answer out of him! When I asked my boyfriend this question he replied he still had a crush on his teacher, in his words “She is still fine!”

18How did you spend your summers when you were a kid?

Summers were the best part of your life when you were a kid! Who doesn’t remember the awful summer you had to vacation with your weird relatives, or playing hide-and-go-seek with your friends. Was there a snowcone stand down the street? Was your mom a teacher and you got to spend all summer with her? Everyone has a different experience. Who knows, maybe a funny story or two will show up.

19Were your siblings mean to you/ were you mean to your siblings?

My boyfriend has a hilarious story about his older sisters accidentally knocking him out with a phone. Don’t worry he’s okay. Siblings are brutal and I promise he will have some great stories to show for the scars.

20What is the worst thing you/your siblings do when you were a kid?

This one involves him or him and his siblings working together to do something his parents still can’t get over. Or maybe his parents don’t know. Did he squirt katsup all over the sweater Grandma Pat knitted him? Did he accidentally turn the dryer on with the cat inside. Kids get in trouble, it’s just their nature. Hearing the worst of the worst is bound to be a little surprising, hilarious, or both.



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