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50 Ways To Ask Someone Out

50 Ways To Ask Someone Out

By Anthony DeVito

1. Ask him in person.

2. Do it over the phone.

3. Write her a letter from the future as if you’re both married. Then, ask her out and inform her, should she say no, that it will disrupt the natural order of things.

4. Send a carrier pigeon to his bedroom window.

5. Email yourself a reminder to ask out the most beautiful person in the world. Then, “accidentally” include her on the email.

6. Send a text message.

7. Hire a celebrity to ask him for you. What’s more impressive than Billy Ray Cirus!

8. Write it in the sky.

9. Hire a mariachi band and serenade her. First thing in the morning.

10. When you ask him out, remind him you only have 24 hours to live. Do this everyday for the rest of your life.

11. Send flowers. BOOM.

12. Hand him his favorite book. On the dedication page, write over the typed text and dedicate the book to “our first date.”

13. Start planning a heist together. Drop the heist idea, and instead ask her to get pizza.

14. Start following him on Twitter. Continue following him in real life.

15. Call in to a local radio station.

16. Hand her two sets of keys and tell her one is for your heart, and the other is stolen from the janitor.

17. Get into his chemistry class and become his lab partner.

18. Make a YouTube video and then send her a private link.

19. Write a letter.

20. Buy her a puppy, but beforehand train the dog to ask her out.

21. Fly him to Paris and ask him in front of the Eiffel Tower. If that doesn’t work, he's stupid.

22. Get the whole school involved. Make everyone take the day off and when she walks into school, you’re the only one there. Holding a dozen roses. This is another one where if it doesn’t work, she's stupid.

23. Send a Facebook message.

24. Tell him how you love scary movies, but are terrified of watching them alone.

25. Tell them you need help with your homework. Make sure you are enrolled in school for this to work.

26. Ask her to meet you at a party. Clarify "meet" is spelled with two "e"s.

27. Place a walkie talkie somewhere in his bedroom. Then, while he sleep repeatedly ask them out.  This will seep into his subconscious, so when you ask him in real life, it won’t be a big deal.

28. Make a Vine.

29. Invite her to one of your extracurricular activities. Toenail trimming does not count, but Toenail Trimming Club totally does.

30. The next time you see him, talk for fifteen minutes straight, without interruption. After, grab your throat and say, “So much talking. I’m parched, what do you say we grab a milkshake? Two straws.”

31. Talking parrot.

32. Put a note in her sandwich.

33. Put a message in a bottle, then throw it in his bathtub.

34. Stuff yourself inside her locker while holding a single, white rose.

35. Ask him to help you with lines from a script. Hand him a fake script in which you ask him out and he says yes.

36. Do the old fashioned “fruit and suit.”  Its where you wear a suit and hand her some fruit.

37. Buy him a cell phone with only one number inside it: yours.

38. Hire a magician who steals her watch. Then say you’re an even better magician, but you’re focus is stealing her heart.

39. Buy him an iPod with only one song inside it: your song.

40. Write him a song.

41. Write her a poem.

42. Make him a portrait.

43. Buy her a heart-shaped locket with two frames. Put your picture in one frame, and in the other frame... a picture of Grumpy Cat.

44. Buy him a cat and then explain that if you had nine lives you’d want to spend all those lives with him.

45. Buy her a dog and explain that “man’s best girlfriend” should also have “man’s best friend.”

46. Bake him a cake.

47. Hand her a clock and then say, “It’s TIME for me to make my move.”  Then, go for the kiss.

48. Do it at a loud concert. That way, if he says no, you can just say, “Go out with me?  No, I said do you want to doubt a tree?” Then, for an hour and half talk about how you don’t think trees are real.

49. Throw a rock at her with an attached note.

50. Spill something on his pants. Offer to wash them. Before you return them, stuff the pockets with rose petals.

What are your creative ways for asking someone out?

Topics: Life
Tags: relationships, flirting, dating, crushes, awkward situations, lists, guys, asking out, 50 lists

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About the Author
Anthony DeVito

Anthony DeVito is a NYC based comic. Originally from New Jersey, he was featured as one of the "New Faces" at the 2012 Montreal Just for Laughs Festival, recently taped a Gotham Comedy Live on AXS TV, performed at the 2013 Bridgetown Comedy Festival and 2013 SF Sketchfest, and is also the former host of "Say What?!" on the NOC TV. You can follow him on Twitter @anthonydevito_

Wanna contact a writer or editor? Email contribute@sparknotes.com.