Loverboy (1989)

Loverboy is the kind of breezy, slightly naughty late-’80s comedy that shouldn’t work on paper, but does—because it’s directed with a light touch by Joan Micklin Silver and powered by Patrick Dempsey’s effortless charm. The movie rides an absurd premise like a well-timed punchline, mixing sweet romantic energy with a steady stream of slapstick misunderstandings and knowing wit, never lingering long enough to turn mean or sleazy. What really sells it is the ensemble: the women Randy meets aren’t just punchlines, and the parental chaos at home gives the film a warm, sitcom-sparked heartbeat. If you’re allergic to sex-farce setups or want a more grounded romance, this may feel fluffy, but if you’re on the fence, it’s an easy, good-natured watch that knows exactly how to keep you smiling.

Loverboy wants to be a cheeky, sex-positive ’80s rom-com about a broke college slacker stumbling into an “extra anchovies” escort hustle and learning a few lessons about desire and adulthood along the way. The problem is the premise is so aggressively silly that the movie leans into broad farce, and the script often feels like it’s chasing setups and misunderstandings rather than building real comedy or romance. Patrick Dempsey is likable, but the film asks you to buy him as an irresistible fantasy for a parade of lonely women, and if that doesn’t click, the whole thing collapses into tacky sitcom energy. If you’re in the mood for lightweight, mildly naughty nostalgia with a few charming moments and a director trying to keep things humane, you might coast along; if you want sharp writing, believable chemistry, or anything subtler than “sex comedy with a gimmick,” this probably isn’t your delivery.