When it comes to Hollywood, there’s a lot to be jealous of — red carpet gowns, adoring fans, a million likes on even the lamest Instagram you throw up, becoming half of a super-hot celebrity couple. But there are some things that aren’t so enviable, like getting stuck working with your ex even after you’ve broken up. Across the music, movies, and TV industry, there are actually a lot of exes who worked together both before and after they called it quits — and, yeah, it gets awkward. 

It’s especially awkward when you’re playing a character that it’s in a relationship, and life starts imitating art off-screen, then you and your on-screen boyfriend break up, and you still have to make out and gaze lovingly into each other’s eyes every week. Blake Lively and Penn Badgley know what we’re talking about, but they’re hardly the only ones. Check out the gallery below to see all the celebrity couples who worked together even after their breakup.