25 Creative Ways to Ask Your Crush out ...

By Diana

25 Creative Ways to Ask Your Crush out ...

If you’ve been falling over a guy for ages, there are tons of creative ways to ask your crush out. Whether you’re artsy, sporty, or somewhere in between, I’ve rounded up a few ideas for you (because I don’t believe in waiting around for him to make the first move). With these 25 adorable ways to ask him out, you’ll bag your crush in no time. Get ready to take a trip to Couplesville with the guy of your dreams!

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Write a Note

With texting a prominent method of communication nowadays, you might want a more thoughtful and personal way to ask your crush out. I’d write him a cutesy note and slip it into his pocket, backpack, or notebook. It’ll be quite the special discovery – even better than finding a forgotten $20 bill.


Sing It, Girl!

If you’re a decent singer, host a karaoke party with your besties and your crush (bribe him with pizza. It works, I promise.). When it’s your turn to belt out a tune, choose a love song and sing it to him. If that doesn’t clue him in, nothing will. If you receive the desired response (i.e. he’s smiling), ask him out right before he leaves for the night. Just remember: music changes lives.


Schedule a Tutoring Session

A tried and true way to ask your crush out is to schedule a tutoring session. When he arrives at your home, lead him to a table with fresh flowers and takeout. Write “will you go out with me?” in your notebook when he’s not looking. Then, tell him you need help with your question. With any luck, you’ll get your desired answer – and maybe even a smooch right then and there!


Paint a Picture

If you’re an artsy kind of gal, use your next art class to paint him a picture he’ll never forget. Asking him out through a work of art is priceless. Are you ready to be the girl who’s always on his mind? Yeah, I thought so.


Stick a Message on the Fridge

If he knows that you’re a major foodie and love whipping up tasty treats, tell him that your refrigerator suddenly stopped working. Before he arrives to take a look at your “broken” fridge, place word magnets at the top of the door. Obviously, the words should form a question along the lines of “want to go on a date?” but you can personalize the message as much as you want. A word of advice: make sure you have enough magnets and that the message isn’t too long! You won’t want to confuse him or overdo it. You’ll have all the kitchen help you need in no time!

Famous Quotes

Silence at the proper season is wisdom, and better than any speech.


Play Monopoly

If you’re a fan of board games and your potential guy has a sense of humor, you can use game pieces as a way to ask your crush out. You can transform Monopoly money, for example, into a creative part of your dating game. Pen a short message on the faux bill, drop it on the floor when he’s not looking, and then tell him that he’s dropped something. Smile and walk away. If you get a text soon after, you’ll know you’ve won that round.


Put a Wrap on It

If you’ll be attending a party and know that your crush will drop in, design a label asking him out. Slap it across a soda or beer bottle and hand it to him when he starts looking at the drinks table. The gesture is totally flirty, and with you in your best pair of heels and just-made-up face, how could he resist?


Hit a Home Run

If you need a way to ask your sports-loving crush out, walk up to him during the next baseball game you’ll all watching at your local watering hole. Flash him a sexy smile and hand him a baseball with your signature and phone number on it. Then, tell him that you’d like to start at first base with him sometime, minus the team and cheering crowds.



Literally. If you’re on the cheerleading squad, get your best buds together and work on a routine that’ll blow him away. Of course, you’ll have the starring part – and probably even the lead guy!


Map It out

One of the most creative ways to ask a crush out involves a bit of a treasure hunt. Give him a map with four of his favorite places marked with an “X”. Explain to him that he needs to visit each place to collect the clues and win an amazing prize. Have three of your gal pals wait at each spot with note cards reading “GO”, “OUT”, and “WITH”, respectively. You’ll be at the fourth spot with a “ME?” in your hand and a bright smile on your face. Treasure found!



An adorable way to ask a crush out is to wait for his special day to do it (provided it’s not too far off!). Hand him a card in class asking him to meet you after school for his best present yet. Meet him outside with a homemade cake asking, “date me?” Scrumptious cake and a gorgeous girl? It’ll be his best birthday yet!


Pick Him up

If he doesn’t own a car just yet, offer to drive him to his next volleyball meet. Stop right in front of his house, a sign with his name on it in hand. When you see him inching toward you, flip the sign over to display your asking-him-out message. Can you say cute?


Play Dress up

If you develop a crush just before Halloween, I have a creative way to ask him out. Dress up as his favorite comic book heroine or female sports star (you get the idea) and iron on “go out with me?” on the back of your costume. Make sure he’ll be spending at least part of Halloween answering the door and ring his bell with a Trick or Treat bag in hand. When he sees you, spin around to display your message. Who knows? Maybe you’ll even end up watching spooky movies at his place that same night!


Give Him a Package Deal

This one’s an easy way to ask a crush out. Place a note titled “Guess Your Crush” in a box decorated with the things you like. List a few clues alluding to who you are to help him along and leave the box on his porch. If he calls you, he’s been paying attention.


Watch the Stars

If you and your potential guy are proud to be geeky-chic, tell him that your backyard is prime stargazing space. When you both lie down and get comfy, point to a big and bright star and exclaim, “I wished for you!” You’ll tell your BFFs that story for ages!


Puzzle Him

If your crush is the type of guy who has enough patience to put a puzzle together, here’s a darling way to ask him out. Buy a cardboard puzzle at your local crafts store and paint it his favorite color. Add your pickup line in with a permanent marker or black paint. Break up the puzzle and place the pieces in a tin. All that’s left to do is pass it on to him and hope he puts the pieces together.


Start with a Kiss

A Hersey’s Kiss, that is. The next time he has the munchies (as in, anytime), hand him a bag of Kisses. But don’t give it up until you’ve added a special message to each strip of paper sticking out at the top of each chocolate. It’ll be a sweet treat –in more ways than one!


Shoot a Video

If you’re looking for a way to ask your crush out but are too shy to do it in-person, a video can work wonders. All you need is a camera or phone with video-shooting capabilities. When you’re finished with your pitch (be sure to look your best!), send it to him via e-mail and keep your fingers crossed.



This is a fun one! Write your invitation on a very tiny piece of paper, then wrap it in a tiny box, now wrap that box in a little bit larger box, and again and again. Make sure that each one is wrapped individually before placing it in the next size. Put a note or a card on it that says something like, "I'd be honored by your 'presents' at (fill in blank)" or "Good things come in small packages." They might get annoyed opening it, but the pay off may be worth it.


Parking Ticket

Print and cut out a piece of paper that looks like a parking ticket. On it make sure to write your date proposal across the top. Then you should sign your name, making sure to include a date, time and place for the "summons" a.k.a how this person should respond to your question. Go ahead and stick it on his/her windshield. This is sure to get some attention!


Radio Station

Call your crush's favorite radio station and request a song. Have them announce your request at a time you know that your crush is listening and make sure the DJ dedicates the song to him/her! Then have the DJ relay your question over the airwaves like "will you go out with (your name here?)" How cute would that be?!


Say Anything

Who doesn't know the iconic scene from the movie "Say Anything?!" Why not go to your crushes house or apartment and pull this same stunt. Make sure you play their favorite song so that you get the attention you want. After he/she looks out the window, put down the radio (or speakers) and ask him/her out!


Message in a Bottle

For this one you'll need some supplies. Get a hold of a small bottle, some sand, and a piece of paper. After you have your supplies, write your invitation on the paper and roll it up! Put the note inside of the bottle with the sand and send it to your crush. What a cute story you'll both get to tell about how you asked him/her out on your first date!



If you can bake and decorate pretty well, this one is for you! Bake some cookies because who doesn't love cookies and then when you decorate them, write a message on them. They're may not be that much room so write small or bake big cookies! The cookies can ask if your crush would like to go on a date or you could ask them specifically to a movie or dinner. This is a fun, yummy, and creative way to ask someone out!



I'd love this one to happen to me! Call or go to your local pizzeria and tell them how you want to ask your crush out. Ask them if they can spell out a word like "date?," "movie?," "prom?," etc. out in pepperoni, mushrooms, or anything else small they can use. Then have them deliver the pizza to your crush's house and make sure he/she knows who it came from!

Now that you’ve learned a few creative ways to ask your crush out, which of these methods are you planning to try out? What are some of your own ways to ask a guy out?

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Feedback Junction

Where Thoughts and Opinions Converge

Hey! I have a crush on my best guy friend. We talk a lot in school and stuff and he hugs me when we meet. I think he flirts with me too. Some people say he likes me a little bit. My sister even told him I liked him but he didn't say anything. Also I txtd him every couple days but he hasn't replayed. What do I do?

Only if I wasn't such a wimp... He should just ask you first

Love 15

I am crushing on this guy called Aaron, thing is, the next time I see him is in April. Should I make the move and kiss him? I'm worried he wont like me back or kiss me back...

Please help me!!!!

I am 12 and shy and crushing on they coolest guy in school

BTW I really love josh toll! You people dont know who he is but he means the world to me!