After fast-paced New York City high-end real estate broker Fiona Rangely (Lacey Chabert) gets dumped by her boyfriend, she escapes to her family’s quaint Vermont Inn for a few days to slow down and evaluate her life. When her ex-boyfriend Nate shows up at the Inn with a brand new girlfriend, Fiona quickly devises a plan to win him back: pretend the handsome and very laid- back head chef Derek (Carlo Marks) is her new boyfriend! Much to the surprise of Derek –and to Fiona herself– in pretending to be in love, she realizes that she’s been thrown a curveball: sometimes the best things in life are worth the wait.
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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.
Terrence J. stars as Charlie, a playboy who’s convinced that relationships are dead. His two best friends, Donald Faison and Robert C. Riley, bet him that if he sticks to one woman for one month, he’s bound to get attached. Charlie denies this until he crosses paths with the beautiful and mysterious Eva, played by singer/actress Cassie. They may agree to a casual affair, but eventually Charlie is questioning whether he may actually want more.