At forty, darkly funny stand-up comic, Shawn Sullivan has bottomed out in the throes of a mid-life crisis. His commitment phobia and fear of success leave him ripe for an Internet prank played by his older, misogynistic brother, Mick. Mick blind-dates the “female” photo shopped Shawn with an attractive bisexual woman, Lane Gold whom Mick finds on a gay dating site. Lane, a thirty-five year old hip and successful pop songwriter, has sworn off men. Her lesbian neighbor, Casey, encourages Lane to seek her soul mate in the gay community.
The ill-fated blind date turns into a stage performance with both Shawn and Lane trading barbs. They are a hit comedy duo and Shawn begs Lane to perform with him. She makes a deal with him. If he will attend gay and lesbian events to overcome his homophobia, she will be part of his comedy act. She also demands, ironically, that Shawn help her and Dylan, her sixteen year old son, with his Eagle Scout Project and the homophobic Boy Scout adventures. Dylan saves Shawn’s life on a rafting trip, and Shawn saves Dylan’s life at his high school wrestling match when the opponent utters a gender slur about Lane. The three leading characters become a family, but when Lane proposes marriage, Shawn begs off, stating that he is a lone wolf. When Shawn won’t commit to marry Lane, she breaks up with him, retreats to the lesbian world and finds a girlfriend, the beautiful Corinne. Lane and Corinne develop a serious attachment.
Dylan, disconsolate over losing his father figure, friend, and his mother’s last chance to be straight, concocts a whacky New Year’s Eve scheme to dress Shawn in drag to gain access to a lesbian party in Hollywood. At midnight, Shawn proposes to Lane in front of all of the women, and chases the fleeing Lane down Hollywood Boulevard in his stilettos. Lane, a strong woman, agrees to accept Shawn’s style of commitment in a surprising, heartwarming and unconventional ending.
This comedy of genders has unique characters that are sympathetic and fascinating. Full of observational comedy and farce, this hilarious tale of two people who become intertwined by fate and random chaos, reaffirms the universal quest for commitment to true love.