A womanizing man-child binges on sex and alcohol, experiments with ayahuasca for addiction therapy and comes to terms with past mistakes.
During a trip to his home state during the holidays a philandering playwright, hometown hero Jake Hudson, engages in a series of casual affairs. A performance problem, followed by a drunk driving incident leads to some soul searching and ultimately the realization that the woman he left behind just may have been the one who got away.
Floundering stand-up performer Jake Hudson, who gained notoriety by performing a one-man show in the nude, returns to his old stomping grounds for a visit during the winter holidays. As the one guy from his small town who made it big, getting women is like shooting fish in a barrel; within the first three days of his arrival he beds an aspiring actress, a chamber maid and a bar bimbo!
The affairs seem to have little significance, except to show that Jake is addicted to the pervasive "swipe right" culture. However, these trysts put in motion some inner turmoil (why can't he get it up for Jillian?) and also create an external threat to his recent ex-wife, Octavia (who is afflicted with Multiple Sclerosis) when a jealous husband comes searching for him at her house which is also his old address. The silver lining is that this event eventually brings the two closer together to suture up some old wounds, but not before Jake hits some personal speed bumps.
Things start to take a turn for the worse when a miscommunication with a pretty young prospect leads to an embarrassing situation for Jake, catapulting the man-child into a tailspin that culminates in yet another late-night sex and alcohol binge which ends where the film begins; with Jake being pulled over in a snowstorm by a salty female cop.
He meets an unlikely friend, Abby, a sex addict, and a self-described "empath" at a mandatory AA meeting. She encourages him to seek alternative therapy in the form of an ayahuasca retreat. A veritable "trip" unlocks some memories that help him come to terms with emotional scars and past mistakes. Just when he's beginning to turn things around he's dealt another blow, forcing him to dig even deeper into his psyche, revealing his anger at a nonexistent God.
There is redemption for Jake, but it's bittersweet as he pours his heart out to Octavia in the nick of time. His only choice is to start his life over with a new one man show; this time fully clothed on the outside, but with some naked self-awareness he previously lacked.
