Poised (2011)

Dr. Harry Thomson's endless therapy dealing with his inability to maintain a relationship is put to the text when he meets Abigail Hastings, a lawyer living across the hall. He's ready to ask her out until he learns that his psychiatrist, Nina Shapiro, has been encouraging him to avoid dating because she's in love with him. Harry's dates Abigail until his anxieties drive him to promptly end his first serious relationship. This plunges him into an emotional tailspin. Things grow more tense when he arrives at a party attended by both Abigail and Nina. Harry is both encouraged and confused when his eccentric family gives him relationship advice. Once Abigail helps him battle through his hesitation they find happiness.