Alex and Mark are watching football when Whitney comes home late from work. She was out to dinner with her work friend, Craig, and afterwards they hit up a karaoke bar for some off-key singing. Whitney's phone rings; it's Craig calling. Alex and Mark quizzically look at Whitney as she laughs about something Craig said over the phone. Mark finally interjects and tells Whiney that her "work friend" has a crush on her. Alex agrees with Mark; he asks Whitney if Craig knows she has a boyfriend, "one that looks and may possibly be tough." Whitney tells them that Craig and she are just friends, nothing more. Craig even has a girlfriend named Marcine. Alex laughs at such an obvious made-up name. Whitney intends to prove Alex wrong by scheduling a double date so everyone can meet face to face.
The following week at Lily and Neal's apartment, Roxanne sits in agony as she waits for game night to begin. "What is it about couples when they've been together for a year? The need to host game nights becomes all-consuming," Roxanne quips. Mark gives Roxanne the competitive eye; he takes game night very seriously. Lily and Neal are one team while Mark and Roxanne are the other. Mark is dubious that Roxanne and he can win because he thinks women have inferior intellects. Roxanne proves him wrong as she answers all of the word association questions correctly while Lily and Neal fail to get one answer right. Later, Lily is worried about her and Neal's performance at game night. Neal tries to qualm her worries by saying it was just a game, but Lily feels it shows a deeper disconnect that they're not on the same wavelength. Lily begins the word association game again, and to her dismay, they fail to get one answer right.
At the therapist office, Whitney finishes explaining to Dr. Grant why they are seeking his help. Dr. Grant mentions that Whitney has been talking for 27 straight minutes, which tells him volumes more then the actual words she's spoken. He asks Alex to repeat the last sentence that Whitney said, but Alex can't remember. As Dr. Grant "digs through the salad of words for the crouton of truth," he theorizes that Whitney is having an "emotional affair" with Craig at the expense of Alex's needs. "Emotional?" Whitney questions. "What a waste of an affair." Dr. Grant gives them exercises to do at home to help improve their emotional intimacy and communication. The exercises are designed to find out how comfortable they are with each other's silences. He then asks them to embrace for 60 seconds with no talking. They awkwardly hug closer and closer, until Dr. Grant asks if they can feel each other coming together. Whitney responds back, "That almost never happens."
Later at the apartment, Whitney and Alex start Dr. Grant's communication exercises. Alex puts on noise canceling headphones in order to guess Whitney's emotions through her body language. Whitney gestures that she's feeling happy, but Alex thinks she's feeling pissed off. Whitney tries again and over exaggerates her body language to show she's happy, but Alex thinks she's extremely livid. Finally, Whitney throws her hands up in the air in extreme frustration, which Alex then guesses is her showing happiness. Later during a trust exercise, Whitney wears a blindfold as Alex calls out instructions on where she should walk. Whitney moves at a snail's pace, not fully trusting Alex's commands. Whitney's cell phone rings, but Alex warns her not to pick it up, as one of Dr. Grant's rules was no cell phone use. Not listening to Alex, Whitney answers the phone and finds an automated message from Dr. Grant admonishing them for picking up and as a penalty tells them to start all the exercises over.
Whitney and Alex have their double date with Craig and Marcine, except Marcine gets sick at the last second and can't make it. So their double date has turned into an awkward threesome as Alex is left behind in the conversation. Whitney attempts to steer the conversation to what Alex and Craig have in common, but Craig always one-ups Alex on the accomplishments of their shared interests. Later at a bar, Whitney tells Roxanne that Alex is jealous of Craig. Roxanne advises Whitney that she needs to do the hard work it takes to squash Alex's concerns or else the relationship can start to break. Roxanne recommends a couple's therapist that saved another friend's relationship. Whitney moans at the possibility of hard work, "I'm not going to therapy unless I know I can win."
Whitney and Alex start a new exercise where they have to tell each other a story from their past that they haven't told before. Alex tries several stories, but Whitney has heard them all. Alex gets upset and worries that these exercises are not helping but making things worse. Whitney tries to calm him down, but Alex stays uncharacteristically livid. He tells Whitney that when they first started dating they agreed that if they ever got bored with each other they would end the relationship and move on. Now Alex is worried that their relationship has reached that point of boredom, and she'll leave him. Whitney reassures him that she's not bored, but Alex feels that she's found someone more interesting in Craig. Whitney holds Alex lovingly and says that deal was made three years ago before she was ever in a real committed relationship; she doesn't feel that way anymore. Whitney and Alex rekindle their love and head to their "boring bed" for some "boring sex."
At Lily's apartment for a game night rematch, Roxanne tells Lily that Mark feels they won the other week because she thinks like a man. Roxanne asks Lily if she agrees. Lily awkwardly backs off from the question, but finally confirms that she does feel safer when Roxanne's next to her in crowds. As Mark starts the word association game, Roxanne purposely throws her answers, while Lily jumps in excitement as Neal and she get every word right. Later, Mark confronts Roxanne about why she's purposely losing the game. Roxanne denies the accusation; she is just letting her feminine side surface. Mark apologizes for telling her that she acts like a man; he meant it as a compliment. Guys find that sexy in a woman because they can relate to her. Roxanne fires back at Mark that he acts more like a woman than she does; he tans, journals and dyes his hair. Mark angrily yells out that the next round will be guys versus girls. He walks up to Neal and tells him they need to beat the girls. Neal tells him not to worry; he memorized all the cards to calm Lily's out-of-sync nerves.
Whitney and Alex meet with Dr. Grant and thank him for his advice. With his relationship exercises, their love is newly refreshed. However, Dr. Grant thinks they still need work and offers them more ways to fix their relationship. Whitney tells him that he's not listening to her and knows exactly how to fix the situation. She walks up to Dr. Grant and sits in his lap for a 60-second embrace. As they hug, Dr. Grant gently relaxes.