At twenty-four, Elliott Roux is what some might call privileged. She comes from a wealthy Boston family and adores her grandmother. The best part of her week is when the two of them have Sunday brunch together in The Public Garden and watch the swan boats. Elliott has a close-knit group of friends, loves her roommates, has a decent job downtown that doesn't require much effort, and adores her city. But while her life may seem perfect on the surface, her family is falling apart and she feels like she doesn't know her mother anymore, maybe never did. And then there's the issue of men. Elliott is always dating the wrong guys. They seem normal on the first date, but she feels like she brings out the crazy in them. Like the guy who confessed to being an adrenaline junkie, who thought it fun to taser himself. Or the stage-five clinger who suggested on their third date, with no hint of sarcasm, that they get a dog together. Despite her bad luck, Elliott isn't about to give up on dating. After all, bad dates make for fantastic stories. And really, what's better than reminiscing with girlfriends over brunch, recounting dates gone awry? It's just a question of whether Elliott can find a balance between her friends, her family drama, and the social scene in Boston. She is nothing if not determined, and sometimes you have to kiss a few frogs before you find your prince.