As if going out with your ex-sister-in-law wasn't awkward enough, Mickey (Woody Allen) and Holly (Dianne Wiest) quickly discover that, even though they've known each other for a while, they have nothing in common. She's a floundering former addict who likes to party. He's a straight-laced hypochondriac who likes to whine.

But all turns out well in the end; after a disastrous first date (which Mickey describes as "like the Nuremberg Trial") the two reconnect and eventually marry.