Editor #21
You might not be as clueless as you think. It probably depends on the girl that you want to ask to prom. But equally as important to the equation is the type of guy that you are. If you have never asked a girl to prom before, then it is best to plan ahead. After all, you have about one month until the big night—one month that will pass by in a heartbeat if you are a busy guy who, on top of prom plans, has schoolwork and other activities.
There is no specific window of time in which you must ask a girl to prom. If you are positive that she will accept your offer, then I think that at least two weeks prior to April 20th is appropriate. However, if the girl you are asking is not necessarily a slam dunk in terms of saying “yes,” then you should investigate her plans first. For a girl you do not know as well, you should probably plan a month in advance.
When it is convenient or comfortable for both you and her, simply ask the girl if she is thinking about going to prom. If she responds with a “no,” do not try to make further plans to ask her. It is better to respect her decision. This will save you from an awkward rejection and her from feeling guilty. Your idea of surprising her with a “promposal” might seem to you like the boldest and most brilliant idea, but to her it could be the biggest embarrassment ever.
If she says she is thinking about attending prom, then you can ask her if she thinks anyone might ask her. Do not be invasive! Girls can easily become suspicious of guys based on the conversations they have with them. You just need to be careful and know when to stop if the girl does not want you to ask her to prom.
It is a different story if you know the girl very well. If you are asking a good friend, best friend or girlfriend to prom, then the asking will be a lot less nerve-wracking and stressful because there is a bigger likelihood that she will say yes.
As for ways that you should ask a girl to prom, I do not think you have to make it a prelude to a wedding proposal like some guys do. In fact, just have fun with it! If she likes you well enough, then any way that you decide to ask her will be appreciated. Cleverness and thoughtfulness are two principles that will never hurt in convincing a girl, in addition to your special talents and skills. Depending on what you think she would react to the best, you should first decide whether you will ask her at school or outside of school.