Before you get yourself into a bind on prom night, because you've asked him and now things aren't working out the way you expected, take a moment to consider the following questions. If you answer them truthfully, it will help you focus on exactly what you want from your date prom night. And if you know this, it may help you avoid unnecessary discomfort or heartache that night. It may even turn that night into the magical evening you've been dreaming about for so long. So take some time to go through these questions and think seriously about them. Write your answers on paper, as well as including reasons for why you chose that answer:
1. How well do you know him. Choose the one that most closely resembles the relationship (or lack of one) that you have with the guy you want to ask:
2. What's his attitude toward you? How do you think he sees you?
3. What sort of arrangement do you want to have with him prom night?
There's no one right answer for any of the above. The thing is to find the answer that most closely matches what you want, because once you have this answer, you'll know several things:
First, you'll know what you're up against when it comes time to ask him.
For example, if you've been dating for more than a year, then it will be easy to ask him, except that you might have this problem: since he knows you well, he might say he doesn't like prom & formals, and that he's not interested in going. Or for example, if you are really good friends, then you will have to decide what you want out of prom night with him: are you going to go to prom with him but still stay really good friends, or do you think you'll probably hook up prom night? Or, if you ask him and you're really good friends, will this throw your friendship off balance if he thinks you like him as more than a friend, but he doesn't have the same feelings for you?
Second, you will also know how you should ask him.
For example, if the two of you are already going out, then you can totally ask him romantically and be very intimate about it (ahem). Or, if you know that the two of you will hook up prom night--or right after you ask him to prom--then you can also be romantic in the way you ask him, although you probably won't want to be intimate. If, on the other hand, you're worried that he might not like you the way you like him, then you want to ask him in such a way that he won't "take it wrong," meaning, that could or could not be romantic depending on how he feels.
Third, you will also know what you specifically want to happen on prom night.
This is probably the most important thing to know because you don't a) want to send out the wrong signals, or b) do not yourself want to receive the wrong signals. For example, if you've been friends for years and have decided to go to prom together, it might ruin your friendship--or at least strain it--if you try to push it into more-than-friends only to discover that he's not interested. Or the reverse may be the case, in that he tries to push it into being more-than-friends and you're not interested. Then what do you do? The solution, of course, lies in taking precautions before anything happens. That means, when you ask him to prom, also lay out what you expect of him that night, or what you're hoping for that night. Whatever you do, I always recommend you lay your cards on the table because this way, you don't risk getting hurt later on, whether through rejection, or because he's coming on to you and you don't want that.