My advice - talk to your GF before you do it, not to get her approval, but to let her know. I talked to my wife and she was really supportive - a big help when you make a dramatic change. I went sly in one step - full head of hair (with a small bald spot) to completely smooth over a weekend. I work in a big company and in general the first reaction was "oh wow!" then "it looks good!" Expect a few negative comments, but who cares about those?Go for it - you'll like the change!
I went straight to smooth - had it buzzed down with a zero guard then went home and shaved clean. Try the zero guard to get a sense of what you'll look like. If you like the look, then shave down smooth and see if you like that even better. It's really a matter of personal choice. I go smooth because I like the feel of it.On the practical side, I started shaving with a HeadBlade using HeadSlick. At first, went only with the grain until I got used to using the blade. After a few days, I started going against the grain to get a smoother shave. Now I use an electric to start out and the HeadBlade to finish (only against the grain with the HeadBlade) and I get a super smooth result.