Remember When Patrick Dempsey Was a Nerd in Can’t Buy Me Love

Decades earlier, he’d been making rounds (and pulsating) at Seattle Grace Hospital Grey’s Anatomy, Patrick Dempsey was busy mowing lawns in Can’t Buy Me Love.

Taking its title from the Beatles song of the same name, the 1987 romantic comedy starred Dempsey as Ronald Miller, a high school nerd so desperate to be cool that he proposes to popular girl Cindy Mancini, played by the late Amanda Peterson— money to impersonate his girlfriend. Yes, as hard as it is to believe, McDreamy actually had to pay to get dates in the 1980s.

Even though it didn’t become a hit like some of its fellow teen comedies of that eraYou can’t buy me love— which ultimately grossed just $34 million at the box office—served Dempsey as the main character in the film, and the 56-year-old actor later became the main character of the romantic comic. Grey debuted in 2005.