<Li> Dr. Amy Shaw (Lacey Chabert): A psychologist for the New York Rangers and Danny's girlfriend in season 2 . She cares deeply for Danny but is constantly worried his feelings for Riley will drive him away . She eventually realizes Danny still has feelings for Riley and breaks up with him in the episode "Surprise!". In season 3, Amy shows up and announces that she is engaged to another man . </Li> <Li> Fitch Douglas (Matt Dallas): Son of a millionaire and Riley's boyfriend in season 2 . Fitch does not speak to his family for he feels their money corrupts them . He constantly travels to Africa to help the children and orphanages, having a long distance relationship with Riley . He is seemingly killed in Africa but later turns up alive at his memorial and proposes to Riley . She regretfully declines claiming she is not the one for him . In season 3, he comes back and Riley attempts to make him her rebound to forget Ben . </Li> <Li> Philip Farlow (Christopher O'Shea): A college professor whom Riley briefly dated in season 3 . </Li> <Li> Georgie Farlow (Mallory Jansen): Philip's sister who briefly dated Ben, but later developed feelings for Danny in season 3 . She is a fashion photographer for Vogue magazine . She doesn't like Riley, but begins to accept her for Danny's sake in the episode "Foos it or Lose It". She breaks up with Danny via voicemail at the beginning of season 4 . </Li>

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