When Whitney (Whitney Cummings, "Chelsea Lately") and Alex (Chris D'Elia, "Glory Daze"), 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 (Zoe Lister-Jones, "The Other Guys") and Roxanne (Rhea Seehorn, "The Starter Wife"). Snapping into action she tries to seduce Alex in a sexy costume, but someone winds up in the emergency room. Also starring are Maulik Pancholy (NBC's "30 Rock"), Dan O'Brien ("How I Met Your Mother"). Jane Kaczmarek ("Malcolm in the Middle") guest stars.

When Whitney (Whitney Cummings) realizes that she and Alex (Chris D'Elia) have never gone on an official first date, she comes up with an unusual idea to recreate the past. Taking this very seriously -- as only Whitney can -- she insists that they follow all of the "rules" of a first date, thus the two awkwardly go to dinner and cap off the night by sleeping in separate apartments. This gives Alex and Mark (Dan O'Brien) a rare opportunity for some much needed guy time. Meanwhile, totally embodying a post first date attitude, Whitney and Roxanne (Rhea Seehorn) spend some quality girl time plotting Whitney's next move with the "new guy," but when Lily (Zoe Lister-Jones) finds out what's going on she recruits Neal (Maulik Pancholy) to help her stage a "chance" encounter between the two lovebirds.

After Whitney (Whitney Cummings) catches Alex (Chris D'Elia) checking out a hot girl she begs for him to admit to his wandering eye, but much to Mark's (Dan O'Brien) delight Alex won't fess up. Whitney decides that the best punishment for her boyfriend is the silent treatment. However, she soon realizes that Alex is enjoying his sentence and she begins to plot a new misery making tactic. Meanwhile, Roxanne (Rhea Seehorn), in hopes of making her ex-husband jealous, teams up with Lily (Zoe Lister-Jones) and Neal (Maulik Pancholy) to throw a fake party so that she can take sexy photos to post via social media.

Movie night at home for Whitney (Whitney Cummings) and Alex (Chris D'Elia) ends up as a competition with each other to see who can be more romantic. Meanwhile, Lily (Zoe Lister-Jones) is on edge with anticipation that Neal (Maulik Pancholy) might propose at any minute causing Mark (Dan O'Brien) to embark on a mission to prove that women are more eager to tie the knot then men. Rhea Seehorn also stars.

After an argument over whether or not Alex (Chris D'Elia) uses a condescending "tone," Whitney (Whitney Cummings) decides she is going to catch her boyfriend in the act and enlists Mark's (Dan O'Brien) help. The two scheme to set up a hidden camera in the couple's apartment. Lily (Zoe Lister-Jones), Roxanne (Rhea Seehorn) and Neal (Maulik Pancholy) gather around the television to watch the drama unfold. Later, Alex's brother Brian (Ken Marino, "Party Down") crashes on the couch, and old sibling rivalries come to the surface causing the two brothers to brawl.

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.