When you say it "works infinitely better with a female Bobbie," I wonder a bunch of things, like what productions you've seen and so on. Forgive me but it's the kind of pronouncement I find so troublesome. I've certainly never felt it didn't work terrifically with male Roberts, when the production was good. If you think it works better here, perhaps it does, but then perhaps you feel that Sondheim should have written a different song since you seem to feel that the song should implicate Robert more directly. In any case, I believe it was written with the idea that Robert doesn't hear the song, it's between her and the audience. Certainly that's the way it was done originally, and with Sondheim's evident agreement, although I do feel it wasn't all that clear in 1970 that Robert and Larry weren't hearing it, and I don't think it has to be done that way, despite what the script says.