Ask him to the dance (so he'll actually say "yes")
Obvi your first choice is your crush. If you’re worried he won’t ask you, though, or if maybe you know that he’s way too shy to ever make the first move, it’s definitely time for you to take matters into your own hands. Don’t be afraid ask him yourself!
And you know how they say the worst that could happen is that he could tell you "no"? Well, we say differently. Check out some of these fun, creative ways to pop the question that’ll be sure to have him answering, "Absolutely, yes."
Send a Puppy
If you don’t have a dog of your own, borrow a precious pup from a friend. Or, even better, see if you could sneakily borrow your crush’s own dog (this is the part where it helps to be BFF’s with his sister and/or his mom). Then, tie a note around its collar, and send it over to your crush after school or when he’s walking home. Odds are, he’ll be so enamored by your appreciation for animals – and by the ball of joy barking at his feet – that it won’t even cross his mind to refuse.
Make a Video
Nowadays, interacting through YouTube has been taken to a whole other level. While you don’t have to make your declaration public knowledge, sending your crush a recorded message through text or email – or even through a link to a private video that you posted on the interwebs – can often be the best way to go. For one, this works especially well for people who are shy. You don’t have to actually face your crush in person, but it’s not exactly impersonal either. You also have the option of making it cute or funny – you could play him a song, for example, or deliver a hilarious monologue.
Yep, if a video message could convince Justin Timberlake to go to a dance with this girl, the chances are that your guy will respond positively are looking pretty high too.
You know that age-old saying, "The best way to a man’s heart is through his stomach?" Well, it’s kind of really true. So experiment with cute ways of incorporating some sort of food into your question-asking. And there are definitely plenty of ways.
You could bake a batch of cookies, for example, then ice one word of the question, "Will you go to prom with me?" on each cookie. Stack them on a plate pyramid-style so that the "will" is on top, and he has to eat his way through the pile to get to the "the dance with me"’ on the bottom. Or, if you want to put a fun spin on it: get a cheese pizza delivered to his house. On the outside of the lid, write something like, "I know this is cheesy, but…" Then, on the inside, scribble your question. The possibilities really are endless! One thing’s definite, though: he’s certain to want to be your date to the dance.
This option is the perfect opportunity to put your excellent drawing skills to use. Note: it most definitely requires getting the permission of his parents, or giving them a heads-up at the very least.