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

Co-authored by Cher Gopman and Hannah Madden

Last Updated: May 9, 2025 References

Asking someone out on a date can be nerve wracking—but it doesn’t have to be! By using a little humor while popping the question, you can make your date giggle and (hopefully!) get them to say yes.

Here are 11 different playful, lighthearted ways to ask out your crush.

1

Pass them a note.

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Throw it back to elementary school with a note expressing your feelings. Then write, “Do you like me? Circle Yes or No.” Hopefully, they’ll circle yes, and you can start planning your date!
- This is also a super low-pressure way to ask someone out. If they aren’t feeling it, they can just circle no, and you can both move on.

2

Write it in sidewalk chalk.

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Borrow some fun chalk colors from your little sibling. Write, “Will you go out with me?” in huge letters outside your potential date’s house, then tell them to come outside. They’ll be so surprised, they’ll probably say yes!^{[1]
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- Bonus points if you add a few fun chalk drawings around your question.
- If you don’t want to go to your crush’s house, you could write it in front of your own and then invite them over.

3

Ask with icing.

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Buy a cake or a huge cookie from a bakery. Have them 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 a great option for anyone with a sweet tooth.^{[2]
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- If your date isn’t a fan of treats, you might want to go with a different option.
- If you have the baking skills, you could even whip something up yourself instead of buying it pre-made.

4

Sing them a song.

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Make up a song expressing your feelings. At the end, ask “will you go on a date with me?” Record yourself signing, then send the video via text or DM to your potential date. If they say yes, you can keep the video around forever as a fond memory.
- If you don’t want to make up a song, you could always sing a classic love song and add your question at the end.
- If singing isn’t your thing, try dancing or lip syncing instead.

5

Give them multiple options for your date activity.

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Come up with 2 or 3 things you guys could do on your date. Write them down, then hand your crush the note and have them circle their favorite option. When they give the note back to you, start planning your date!
- Your options could be things like: going to a museum, eating a home-cooked meal, going out to a fancy restaurant, spending a night star-gazing, or going on a nature walk.
- Reader Poll: We asked 2622 wikiHow readers about which first date they’d like to go on the most, and only 8% said going rock climbing. [Take Poll] So, suggesting a more casual activity, like grabbing dinner or seeing a show, might be more fun for your date.

6

Send a gif.

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If you can’t see your crush in person, try asking them over text. Pick out a funny gif that says, “wanna go out?” or “will you be mine?” Text it to them with a few heart emojis to get your point across.^{[3]
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- If they say yes, you can start planning your date! Pick out a time and a place to meet up in person.
- Asking someone out over text isn’t ideal, but it’s great if you live far away or you can’t see each other for a while.

7

Try a cheesy pickup line.

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Make your potential date giggle as you ask them out. Try something with a play on words to really get them going. You could try lines like:^{[4]
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- “Do you like coffee? Because I like you a latte.”
- “Do you have a bandaid? I scraped my knee falling for you.”
- “Are you Australian? Because you meet all of my koala-fications.”

8

Write it on a pizza.

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No one can resist the cheesy goodness of a pizza. Order a fresh pie, then write “Will you go out with me, or is this too cheesy?” on the box before handing it to your potential date. When they open it up, they’ll get a deliciously tasty surprise.
- If they say yes, your first date can be enjoying the pizza that just came to the door.

9

Order a singing telegram.

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Hire someone to show up to their house and sing about them. At the end of their song, the telegram can ask, “Will you go out with ___?” If they say yes, it will be a question they’ll never forget!
- Pick a time when you and your potential will be together, like when you’re hanging out at their house or you’re out at a restaurant.

10

Write it on a stick of gum.

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If your potential date always asks for a piece, it’s the perfect opportunity. Unwrap a piece of gum and write, “Will you go out with me?” on the wrapper. Put it back around the stick of gum, then offer it to them the next time you see each other.^{[5]
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- If you’re worried about your potential date picking the wrong piece of gum, make sure it’s the last one in the pack.

11

Make it a challenge.

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If you’re both competitive, use that to your advantage. Say something like, “I bet you can’t come up with a better date idea than me.” When they explain their idea, you can concede and say something like, “Okay, you win. What time should I pick you up?”^{[6]
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- This is a pretty bold option, so you should only use this one if you’re 99% sure your potential date is interested in you.

Expert Q&A

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Question

How can I tell if someone isn't interested in dating me?

Cher Gopman
Dating Coach
Cher Gopman is the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Cher is a Certified Life Coach, a former psychiatric nurse, and her work has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post.

Cher Gopman

Dating Coach

Expert Answer

Body language is key here. If someone is leaning in and engaged when you're talking to them, that's a sign that they're into you. If they're not leaning in or if they pull away or move when you get closer, that's a sign they're not interested. If they're not asking you questions and just giving you short one-word answers, that's another sign they probably aren't interested in dating. They might be closed off with their arms folded.

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