Lilly, a hard working EMT, is only focused on her job and getting into medical school. So when wealthy slacker Jeff enters her life it throws her off course. At first, Lilly wants nothing to do with Jeff or his sense of entitlement and lack of direction. As she spends more time with him, she starts to realize that you can’t always judge a book by its cover.
After ten years of dating, Chloe’s boyfriend Eric still hasn’t matured. Hoping to give him the push he needs, she dumps him; confident Eric will grow up and beg her to come back. However, six months later, Eric meets Chloe for dinner with big news: he’s getting married in a week. Needing a break to mend her broken heart, Chloe takes a vacation, but when she arrives, she learns that Eric and his fiancée are getting married at the same resort!