While driving, Matt Pandamiglio shares a personal story that begins with his hesitations about moving in with his long-time girlfriend, Abby, after eight years together.
At Janet's engagement party, various family members press him about marriage, which leads to a surprising episode of sleepwalking that night. In a candid exchange, Abby expresses her discomfort with Matt's indifference towards marriage. Reflecting on their relationship dynamics, Matt reveals that he initially pursued her, but Abby has largely driven the relationship's progress. A peculiar discovery awaits him when he finds their TiVo filled with wedding-related shows, prompting a conversation with Janet, who suggests that perhaps Matt and Abby need a little "breather."
At the comedy club where Matt works, he plans to broach the topic of taking time apart, but interruptions come in the form of friends visiting with their baby. Opportunity knocks when his boss, Ron, offers him stage time. After a performance primarily filled with old material, Matt connects with a disgruntled comedian and seeks out their agent, Colleen, thanks to Abby's encouragement.
The night takes a turn when Matt, grappling with his aversion to Abby's baby talk, experiences another sleepwalking incident, resulting in a fall from a dresser. This incident worries his father, who insists that Matt consult a sleep specialist, but Matt brushes off the concern.
Colleen reluctantly meets with Matt and manages to secure him a modest gig at a college upstate. With no other option, Matt skips work only to discover that the school forgot to book a comedian. They offer him a chance to emcee a lip sync contest instead. Despite the awkward setting, Matt enjoys getting paid to perform and spending the night at a motel.
The following day brings a chance to open for Marc Mulheren, during which Matt struggles but eventually gets encouraged by Marc to incorporate his relationship experiences into his act. This leads to a successful set, prompting an excited call to Abby, who is out with friends, creating a communication gap that leaves him feeling isolated. He ends up staying on a friend's couch and wakes up unexpectedly in the shower.
As time progresses, Matt hones his act while touring the northeastern U.S. One night, a waitress flirts with him, and they end up having a one-night stand. This infidelity weighs heavily on him, especially at Janet's wedding. When his mother asks about Abby's presence in the wedding pictures, Matt is at a loss for words. After a silent car ride home, Abby returns drunk and suggests they break up if Matt continues to avoid marriage. In a moment of desperation, Matt proposes to her, which she ultimately accepts.
However, Matt's sleepwalking problems worsen, and Abby urges him to seek professional help. Instead of addressing his fears, he channels his experiences into his comedy routine. Abby starts planning their wedding, but one fateful night, a picture from Matt's mother of Abby's wedding dress triggers another sleepwalking episode, leading him to jump out a hotel window. After receiving treatment for his injuries, he tells Abby he doesn't want to get married, resulting in their breakup.
Later, while in his car, Matt reflects on his journey and visits Abby, now happily married with children. He seeks answers about their past, discovering she stayed with him out of compassion. Finally, at a comedy club, Matt performs this very story, revealing to the audience that he sought the help he needed and was diagnosed with REM behavior disorder. Although he still manages his sleep issues with a strict routine and medication, he acknowledges that it's perfectly fine not to be "cured."
