Most Helpful Girl
I'm all for cutting it (every guy I've ever seen with long hair was WAY more attractive, in my opinion, after they cut it short), but I'd advise you against dyeing it jet black. Plain black doesn't look natural on most people unless you already have plain black hair, and if you decide you don't like it, the dye is really, really hard to get out. If you want the look of black without it being so unnatural, try dyeing your hair with a dark BROWN dye. Some of them do get almost black, especially the really dark ones, but it's a lot softer of a color, so it won't clash with your skin tone as much.
(I'm talking based on experience with myself - I have naturally light brown hair and fair skin. If your hair is already pretty dark or you have medium or darker skin, then black is probably not as bad a choice)