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.