Here's one of my all-time Prince favourites. "If I Was Your Girlfriend" was the second single off his 1987 masterpiece Sign O' The Times. It's a Prince pulling all the plugs when wooing his girl, coming off as tender and caring/sex-hungry, shy/brash, etc., using all the tricks in the book. It's also a really good song in itself, of course. True classic!
PS! TLC did a very cool version on their CrazySexyCool album in 1994.