Dear Ace & Luther,
Dear Winfo Worries,
One possibility would be to do the winter formal version of the Promposal. This is a brilliant approach, as long as you enjoy appearing pathetically in need of less free time and more attention. Promposals basically say: “I have no confidence in myself when I’m not dressed like a cartoon character, but might you still want to take pity on me and go to the dance?” Begging for a pity date will never be part of Ace’s repertoire.
I would go with a more straightforward approach. Consider your typical form of communication with your crush. Do you ever text? Talk on the phone? See each other outside of school? Or do you just talk to your crush in school? Whatever the answer is, I would use the same form of communication to ask your crush because it will feel comfortable and natural- unless it’s over text. That feels too wimpy to me. If you do it at school, ask your crush if he/she can go to the other building for a minute, and pop the question during the walk when you have a little privacy.
When you ask, you should simply say, “Would you like to to go winter formal with me?” Don’t get cute; just ask the question. If he/she can’t go for whatever reason, keep your chin high, smile, and say, “No problem, maybe another time,” and remain confident and comfortable in all future social interactions. If the answer’s yes, then have a great time.
Of course there’s a completely different challenge if your crush is someone you barely talk to and secretly admire from afar. If that’s the case, don’t bother asking. Use the next two months to build some kind of connection and then ask the person to prom. I would have zero interest in going to a formal dance with someone who must creepily stare at me throughout the day, although I suppose things worked out for Mr. Thomas and Ms. Northenscold.
Dear Winfo Worries,
I really don’t think you can go wrong adopting a much bolder approach than what Ace has suggested. There are really three reasons why this promposal-style ask is the only viable course of action.
For starters, if you aren’t willing to make a fool of yourself, are you really sure you want to go with this person any more than you just want to go with a group of friends? Put yourself out there in a way that is more creative than cringeworthy, and your crush might just say yes. A soft whisper on the way to Biology is lame and easily shot down. Be bold.
Secondly, making a fool of yourself by dressing up like the Little Mermaid and yelling, “Call me Ariel ‘cause I wanna be part of your world,” will, at the very least, get the attention of a person who otherwise might not even know your name. The effort required might just be enough to turn the “tide” in your favor. You’re smart enough to ask us for advice, so you should be able to come up with something witty and memorable. I mean, who could say no to someone dressed like a Geek Squad employee with a sign that says, “Can I connect to your personal hotspot?”
If, for some reason, your crush doesn’t take the bait, look what you’ve done. You’ve created a name for yourself. There may be any number of other potential dates who are now aware of your cunning wit and fearless passion. You’re marketable. Even if it isn’t the date you set out to get, it’s unlikely you’ll be alone on the night of Winter Formal.
Really the whole thing hinges on confidence. You clearly aren’t confident enough to ask the person on your own, so you need to fake it by going all out. This way you aren’t really just putting yourself out there to him or her specifically, but you’re trying to have fun. People want to be around other people who have fun. Be fun. Don’t be too sentimental here. Get sentimental when you want to be in a relationship. And another piece of advice, if you’re wanting a real relationship with this person, a dance is a terrible way to start. But, if you want to have fun at the dance with a person you like, start the fun with how you ask.