What Are Some Funny Ways to Ask Someone Out on a Date?

It can be nerve-racking to ask someone out on a date—but it doesn’t have to be! You can make your date laugh and (hopefully!) get them to say yes by using humour when popping the question. We’ve compiled a list of some amusing ways to ask your date out to keep the question lighthearted.

1 Give them a note.

Return it to elementary school with a note expressing your emotions. Then type, “Do you like me?” Fill in the blanks with Yes or No.” Hopefully, they’ll say yes, and you’ll be able to start planning your date!

This is also a very low-pressure method of asking someone out. If they don’t like it, they can simply circle no and you can both move on.

2 Make a chalk drawing of it on the sidewalk.

Borrow some bright chalk colours from your younger sibling. Outside your potential date’s house, write “Will you go out with me?” in large letters, then invite them to come outside. They’ll be so taken aback that they’ll probably say yes!

You’ll get extra points if you draw some fun chalk drawings around your question.

If you don’t want to go to your crush’s house, write it in front of your own and invite them over.

3 Make an icing request.

Purchase a cake or a large cookie from a bakery. Write “Will you go on a date with me?” in frosting on the top of the treat, then hand it to your potential date. This is an excellent choice for anyone with a sweet tooth.

If your date isn’t a big fan of sweets, you might want to try something else.

If you have baking skills, you could even make something from scratch instead of buying it ready-made.

4 Sing a song for them.

Make up a song that expresses your emotions. Finally, ask, “Would you like to go on a date with me?” Record yourself signing, then send the video to your potential date via text or DM. If they say yes, you can keep the video as a keepsake for the rest of your life.

If you don’t want to make up a song, you could always sing a classic love song and end with your question.

If singing isn’t your thing, try lip syncing or dancing instead.

5 Provide them with a variety of options for your date activity.

Make a list of two or three things you and your date could do on your date. Write them down, then hand the note to your crush and ask them to circle their favourite option. Begin planning your date as soon as they return the note to you!

Going to a museum, eating a home-cooked meal, going out to a fancy restaurant, stargazing at night, or going on a nature walk are all options.

6 Send a gif.

If you can’t see your crush in person, try texting them. Choose a funny gif that says, “Would you like to go out?” or “Would you like to be mine?” To make your point, text it to them with a few heart emojis.

If they say yes, you can start making plans for your date! Set a time and location for a face-to-face meeting.

Texting someone out isn’t ideal, but it’s great if you live far apart or won’t be able to see each other for a while.

7 Make an attempt at a cheesy pickup line.

Make your prospective date laugh as you ask them out. To really get them going, try something with a play on words. You could say something like, “Do you like coffee?” Because I enjoy a latte with you.”

“Do you have a bandage on hand?” I grazed my knee while falling for you.”

“Are you from Australia?” Because you satisfy all of my koala-fication requirements.”

8 Make a pizza out of it.

A pizza’s cheesy goodness is irresistible. Order a fresh pie, then write on the box, “Will you go out with me, or is this too cheesy?” before handing it to your potential date. When they open it, they will be greeted with a delectably tasty surprise.

If they say yes, your first date will be able to enjoy the pizza that has just arrived at the door.

9 Request a singing telegram.

Hire someone to come to their house and sing a song about them. The telegram can ask at the end of their song, “Will you go out with ?” If they respond positively, it will be a question they will never forget!

Choose a time when you and your potential will be together, such as when you’re at their house or at a restaurant.

10 Make a note of it on a piece of gum.

If your potential date always asks for a piece, this is your chance. Unwrap a piece of gum and write on the wrapper, “Will you go out with me?” Re-wrap it around the stick of gum and offer it to them the next time you see each other.

If you’re concerned that your potential date will choose the wrong piece of gum, make sure it’s the last one in the pack.

11 Make it a contest.

Use your competitiveness to your advantage if you’re both competitive. Say something like, “I’m sure you can’t think of a better date idea than me.” When they explain their concept, you can agree and say something like, “OK, you win.” When should I come to pick you up?”

This is a risky option, so use it only if you’re 99 percent certain your potential date is interested in you.

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