Owen (Michael Angarano) and Hallie (Emma Roberts) have been together for years, but when Owen wavers on Hallie's proposition to move in together, they make the rash decision to call it quits. To both their dismay, they find it especially difficult to truly separate given how intertwined their lives have become. Meanwhile, Owen's best friend Matt (Patrick Gibson) finds himself completely smitten with Hallie's cousin Willa (Dree Hemingway), and they embark on an unexpected, but promising, romance of their own.