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.
When Whitney realizes that she and Alex 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.
After Whitney catches Alex checking out a hot girl she begs for him to admit to his wandering eye, but much to Mark's 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, in hopes of making her ex-husband jealous, teams up with Lily and Neal to throw a fake party so that she can take sexy photos to post via social media.
Movie night at home for Whitney and Alex ends up as a competition with each other to see who can be more romantic. Meanwhile, Lily is on edge with anticipation that Neal might propose at any minute causing Mark to embark on a mission to prove that women are more eager to tie the knot then men.
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.
When Alex encourages Mark 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 steps in for guy's night out, only to run into Mark and his new best friend, Neal. In an effort to reunite the bro-mance, Whitney, following advice from Lily and Roxanne, arms herself with some Rocky Road and red wine and sets out to discover the real root of Mark's heartbreak.
When Whitney and Alex go on a double date with Roxanne, Whitney is surprised to learn that Alex had a full life before he met her. In an effort to do more things together, they decide to play a friendly game of basketball, but things go awry and a sore loser emerges shocking the gang. Meanwhile, Lily thinks that she will win Neal's mother over by embracing his Indian heritage, but she takes it to a whole other level.
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.
Excited for her upcoming nuptials, Lily asks Whitney to be her maid of honor and plan an engagement party for her and her fiancé, Neal. All the party planning stresses Whitney out causing sleepless nights, so Alex suggests that she go see her therapist, Dr. Price for some help -- but a prescribed solution causes even more mayhem. Meanwhile, Roxanne decides to take charge of her potential future and finds an unlikely support system in Mark.
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.