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New York lawyer Ronnie Russo (Neil Brown Jr.) is entangled in a complicated web of conflicting loyalties when summoned to his Boston hometown by a dying childhood friend (Jeremy Sisto). Sent on a mission to fulfill his friend's final wish - a reunion with his estranged son - Russo is forced to confront his past and a secret childhood trauma he's kept hidden for over 25 years.

This is an update of George Bernard Shaw's "Pygmalion" that changes the genders of the main characters. Hannah Higgins attempts to turn blue-collar Boston beer vendor Elliot Doolittle into a viable candidate and inadvertently learns something of Elliot's side of life.

When relaxed and charming Ben Wrightman meets workaholic Lindsey Meeks she finds him sweet and charming, they hit it off and when it is winter Ben can spend every waking hour with Lindsey, but when summer comes around the corner Lindsey discovers Ben's obsession with the Boston Red Sox. She thinks it is perfect until everything goes downhill for them.