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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.
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Whitney catches Alex checking out an attractive woman but he refuses to admit to it; Roxanne tries to make her ex-husband jealous.
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After an argument over whether or not Alex uses a condescending "tone," Whitney decides she is going to catch her boyfriend in the act and enlists Mark's help. The two scheme to set up a hidden camera in the couple's apartment. Lily, Roxanne and Neal gather around the television to watch the drama unfold. Later, Alex's brother Brian crashes on the couch, and old sibling rivalries come to the surface causing the two brothers to brawl.
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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.
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When Alex's childhood dog passes away, Whitney suggests they adopt a dog together. However, the adoption process isn't as easy as they'd hoped especially when dealing with pound owner Mrs. Janks. Meanwhile, Roxanne is interested in some financial advice and Lily, in an effort to bring them closer, suggests working with Neal, but things become increasingly awkward after a sexual mishap during their first meeting.
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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.
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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.