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.
When Alex refuses to share the password to his phone, Whitney, who believes that they should share everything, becomes upset. Deciding they both need some solo time, they each plan a night out without each other -- but when Whitney comes home early she finds Alex in a compromising position. Meanwhile, Lily and Neal move into their new apartment together, but Lily is nervous about being herself, specifically in the bathroom.
Whitney and Lily begin to plan "the perfect" wedding, but Lily's traditional vision for her big day takes Whitney by surprise and ends up causing a riff between the two friends. Meanwhile, Alex enlists Neal to help with some investor meetings so that he can pitch his next great website idea, but he panics when he thinks he might be a one hit wonder. Elsewhere, Roxanne and Mark decide to do a good deed by donating blood however, this good deed might not turn out well for one of them.
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, 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.
When Whitney becomes close to a male co-worker, Alex begins to feels a little jealous. The two notice a disconnect in their relationship and decide to go to see Dr. Grant, a couples therapist who assigns at home exercises designed to improve communication and intimacy -- and result in some awkward moments. Meanwhile, Lily and Neal host a game night and Mark and Roxanne realize that they make good partners.
Whitney is shocked to discover that Roxanne's ex-husband Lance is back in town. Whitney tries to dig up dirt on Lance so that she can convince Roxanne that he is not a changed man, but instead ends up with a surprise of her own. Meanwhile, Neal encounters some racism with one of his work colleagues, but isn't sure how to handle the situation. Elsewhere, Lily doesn't want to tell Neal that she lost her engagement ring and begins frantically searching everywhere for it.
After Mark breaks it off with yet another woman, he shares his personal theory -- explaining that couples know within 48-hours of meeting if they want to be together. Not surprisingly, everyone agrees that they knew they had met their soul mates within that timeframe except Whitney. Trying to prove her wrong, Alex takes Whitney on a trip back to 2008 and the night they first met. While reminiscing, it is discovered that Lily and Roxanne needed some special help to discover that they might actually like each other.
Trying out a new shapelier bra Whitney gets more than she bargains for when she entices Alex with her enhanced look. After Roxanne calls it quits with Lance, she asks Mark to help pack up his stuff, but things become complicated when Mark decides to take advantage of the situation. Meanwhile, Lily and Neal begin discussing a pre-nup, but the conversation leaves them wondering if they should even get married.
When confronted by a mugger Whitney's reaction surprises both she and Alex. After Lily and Neal call off their wedding, Lily enlists her also newly single friend Roxanne to help keep her busy. Meanwhile, Mark tries to be a good friend by letting Neal stay at his place and encourages him to open up about his feelings.
When Whitney (Whitney Cummings) finds a box of stuff from Alex's (Chris D'Elia) old girlfriend in the basement, she confronts Alex about it. Not satisfied with his answers she turns to Mark (Dan O'Brien) and gets more information than she bargained for.
The group realizes that they haven't heard from Neal in a while so Whitney and Alex decide to make a surprise visit to his apartment and find him on what appears to be a date. Trying to be supportive, Whitney has the gang over for dinner, giving Neal the perfect opportunity to break the news to Lily in person.
Alex returns from a bachelor party and makes a drunken marriage proposal to Whitney. She laughs it off, but when she finds out that he broke her one rule about strip clubs -- no going into the Champagne room - she sets out to find Britnee, the dancer who lured him in. The confrontation takes a turn and Alex once again takes a knee. Meanwhile, Lily and Neal continue to figure out their new friendship and Mark begins to realize that he has feelings for Roxanne.