There's a pretty good thread on the Nutty Buddy floating around here, you should definitely find it. I tried a regular cup in compression shorts with a pouch and couldn't stand it. I have the NB now and I really like it. The only down side I can find to this, is that because it's not padded on the edges, there's a sensitive spot on the inside of your groin that the NB can dig into. However, that could be due to my figure. Other than that, the NB is 100 times better than the regular cup I used to have.
NB has money back guarentee, so buy it, put it on in the house, lay on it, wrestle with your girlfriend a little, see how you like it. You don't have anything to lose, and I really can't imagine somebody trying it out, then deciding they'd rather go with a normal cup.