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Wedding planner Sienna Hart is hired to organize the nuptials of her former childhood best friend Matt and his chic fiancé Mindy. The pair get closer as the future bride is distracted by her work. But as the wedding gets closer, Sienna must decide if she is ready to reveal her true feelings before letting Matt go again.

Though Rachel is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy. Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan, Rachel's confidant, harbors a potentially explosive secret of his own.

Mason is a 20-something college graduate grief stricken by his failed attempts at romantic love. He attends a Valentine’s Day party with his best friend Cheryl in hopes of reuniting with his long-time crush, Harvey. Missing his presence and questioning the existence of love, he gets intoxicated unbeknownst to the consequences that are soon to follow.