I asked this very question two years ago before my senior prom. I rolled at my prom and let me just tell you, it was by far one of the best experiences of my life. I danced all night, talked with all my friends there (by the way, all my close friends also rolled that night), I even had some chats with a couple of the teachers there that were chaperoning. Prom was I think at the time my 5-6th time rolling. I did not find it hard at all to keep my shit straight, nor did having to keep my shit straight kill my roll. Is it a huge risk? Definitely. I'm sure you're well aware of what will happen to you if you get caught. In the end, it's all up to you. You decide what's worth taking risks for.
To this day I don't regret it one bit. Even clubs and raves I've gone to since then don't come quite close to how I felt that night (probably from tolerance and whatnot).
PS: I think one of the funniest memories I have of that night is when they frisk you at the door for. I popped my pills in the parking lot and within the 20 minutes it took to get to the door, I started coming up. That frisk felt more like a massage