Barry Burke, portrayed by Tyler Labine, is a young man who struggles in social scenarios, often making him an embarrassment to his married friends. His circle includes Rafe, played by Hayes MacArthur, Kurt, depicted by Thomas Middleditch, and Desmond, who is brought to life by Damon Wayans, Jr.. During Rafe's father's funeral, Barry delivers a questionable eulogy where he recalls their sixth-grade escapades, including a trip to a porn movie and the revelation of Rafe's dad teaching them to smoke weed, before eventually disclosing Rafe’s father was unfaithful while alive.
As Barry's antics start to alienate his friends, he tries to intervene in Kurt's relationship with his demanding girlfriend. Unfortunately, his cluelessness leads to Desmond's dismissal from his job after he makes an inappropriate comment about attractive young women to Desmond's boss, who ends up being the father of one such woman. One day, Barry arrives uninvited at Kurt's home, only to find himself alone and later caught in an embarrassing situation when Kurt arrives unexpectedly with Camille, played by Frankie Shaw.
In a misguided effort to help, Barry's friends decide to find him a wife. They attempt to procure a mail-order bride, but she flees after a disastrous first date. However, fortune turns when Barry meets Melanie Miller, skillfully portrayed by Lucy Punch, at a restaurant. After both encounter mishaps with their respective dates, they quickly develop a connection, reveling in their mutual lack of propriety.
As they embark on a series of dates, Barry's friends initially try to steer them towards acceptable behavior, but they soon capitulate, realizing the futility of their efforts. Interestingly, Barry and Melanie's not-so-innocent relationship inadvertently improves the sex lives of the group. Despite their burgeoning romance, they remain abstinent due to Melanie's unfortunate yeast infection.
The gang then invites Barry and Melanie on a couples' getaway, hoping Barry will moderate his behavior. Instead, Melanie's wild side emerges, much to everyone's shock. Things escalate at Kurt's lodge when Barry and Melanie accidentally set it ablaze during a candlelit rendezvous, pushing the group to their limits. In a moment of frustration, Kurt, joined by Desmond and Rafe, tell Barry they can no longer be friends, leaving him feeling desolate and blaming Melanie for his woes. In turn, Melanie feels hurt and decides to end the relationship.
In the end, clarity washes over the group; Kurt recognizes Camille's manipulation, leading him to break up with her. Desmond contemplates his work-life balance and makes the necessary adjustments. After a heartfelt apology and reconciliation, the friends reunite. Barry realizes he wants to be with Melanie again and pursues her with an overtly romantic, albeit still inappropriate, gesture. Their love story culminates in marriage, marking a new beginning for both of them, full of love and laughter.
