When Whitney and Alex, a happily unmarried couple, attend one of their friends' weddings, Whitney realizes that she and Alex are dangerously close to relationship boredom after three years together. Determined not to let that happen, Whitney consults her close circle of opinionated girlfriends Lily and Roxanne. Snapping into action she tries to seduce Alex in a sexy costume, but someone winds up in the emergency room.

Whitney re-creates the first date she and Alex never had.

Whitney catches Alex checking out an attractive woman but he refuses to admit to it; Roxanne tries to make her ex-husband jealous.

Whitney and Alex have a movie night at home, but the evening soon becomes a competition over who is most romantic. Meanwhile, an edgy Lily anticipates Neal's imminent proposal, sparking Mark's mission to prove that women are more eager to marry than men.

When Alex (Chris D'Elia) encourages Mark (Dan O'Brien) to recycle his beer can, Mark takes an unusually firm stance against it, causing the two to "break-up." Trying to cheer Alex up, Whitney (Whitney Cummings) steps in for guy's night out, only to run into Mark and his new best friend, Neal (Maulik Pancholy). In an effort to reunite the bro-mance, Whitney, following advice from Lily (Zoe Lister-Jones) and Roxanne (Rhea Seehorn), arms herself with some Rocky Road and red wine and sets out to discover the real root of Mark's heartbreak.

When Lily asks Whitney to be her maid of honor and plan her engagement party, the stress drives Whitney to see a therapist; Roxanne decides to take control of her future.

Whitney and Alex scheme a way to skip out on their family gatherings to start new holiday traditions with their friends Lily, Neal, Mark and Roxanne. However, Whitney's little white lie to her mother Candi and an unexpected visit from her father, Vince, cause her perfect plan of merriment to unravel.

Whitney is upset when Alex won't give her the password to his phone; Whitney finds Alex in an awkward position; Lily has jitters about her new living arrangement.

In an effort to help Whitney earn some money, Roxanne hires her to be her assistant and office spy. Willing to do anything to help Roxanne, Whitney befriends Lindsay (Kathy Griffin), the assistant to Roxanne's nemesis, and goes out of her way to appeal to her. Meanwhile, alone at home Alex takes it upon himself to do a little reorganizing. Elsewhere, Mark, who is dealing with a girl problem, enlists the help of Neal and Lily.

Whitney is stunned when she discovers Roxanne's ex-husband is back in town; Neal is unsure of what to do when faced with racisim; Lily loses her engagement ring.

Whitney has an unexpected reaction when confronted with a mugger; Lily tries to keep herself busy after her and Neal's wedding is called off; Mark encourages Neal to talk about his feelings.

Whitney confronts Alex after finding a box of his ex-girlfriend's stuff in the basement; Lily tries to be a perfect roommate.

Whitney and Alex make a surprise visit to Neal's apartment and discover that he appears to be on a date. Whitney invites the gang to dinner so Neal can share his news with Lily.

Alex drunkenly proposes to Whitney after a bachelor party. Mark realizes he has feelings for Roxanne.