It's game night at Sean's place and Sean and Liz are crushing Lorna and Ellie in charades. If a movie isn't Twilight or Step Up, Ellie doesn't have a clue what it is, which causes Lorna to ponder if they'll ever win another game of charades. When Liz abruptly leaves to meet her friend Carl for a date, Sean grows suspicious. Usually Liz always wants Sean to approve of her man candy, so how come it's been three weeks and he's never met this Carl guy? Lorna assumes Carl is a criminal, and Ellie wonders if he even has a face. Off the ridiculously wrong explanations, Sean decides to get to the bottom of this mystery.
Sean finds Liz at the Sam Oliver's restaurant and confronts her. Just as Sean sits down, an over-the-top gay man comes to the table with drinks and begins talking up Liz like they're old friends; it doesn't take Sean long to figure out this guy is Liz's "date," Carl. When Carl goes to get Sean a drink, Sean accuses Liz of cheating on him with another gay man! Doesn't she have any respect for societal norms?! Liz tries to backpedal and explain herself, but Sean isn't having it. Finally, Liz complains that she needs to get out more and right now all Sean does is stay at home and play party games with his family... isn't she allowed to have two gay best friends? Sean scoffs. Of course not!
The next day at work, a popular vendor named Tippy is in the office detailing her Christmas lineup when Max comes in and attempts to showcase his genius for retail. Max knows everyone gives Sean props for identifying trends before they happen, but little does the staff know that Max has the same skill. This year, Max ordered 50 pairs of chain mail pants to capitalize on the recent fantasy craze associated with Game of Thrones and The Lord of the Rings. Everyone knows this is a horrible idea... everyone, that is, except Max. In the break room, Sean bumps into Liz and is still annoyed about the Carl thing. To get back at her, he invites Tippy to take Liz's place as his charades partner later that night, seeing that Tippy is his good friend and all... Liz is annoyed by the revenge tactic.
What started as a means of getting back at Liz soon turns into a nightmare for Sean. The bubbly spirit that Tippy exudes on her seasonal trip to Sean's workplace is not as much fun in a more casual environment. During charades, Tippy slaps Sean multiple times as she pantomimes "Boys Don't Cry" and later pushes him over in an impromptu race to the kitchen for ice cream. When Tippy holds Sean down and sprays whipped cream into his mouth as a gag, Sean realizes he may have a pending hostage situation on his hands. Not surprisingly, Lorna finds Tippy to be wonderful and wonders why it took Sean so long to find a nice friend like her. Tippy is so much better than Liz!
At work, Hunter lets Sean know they've sold exactly zero pairs of chain mail pants since featuring them on the site. When Max comes in and Hunter reveals this unsettling fact, Max pulls Hunter aside and yells at him for humiliating his boss in front of Sean. Max then orders Hunter to participate in a viral marketing campaign for the pants: that night, Max and Hunter will go to all the cool bars downtown and wear the pants, setting off a social media firestorm. Meanwhile, Liz walks into the office with Carl and the two share a laugh over an inside joke. Not to be outdone, Sean pulls Tippy aside and begins fake howling as if she said something hilarious. Sean and Liz both increase the volume of their laughing to get on the other's nerves.
Upset over the laughing competition, Liz takes Sean into his office and comes clean about her friendship with Carl. At first hanging out with Carl was a fun change of pace, but now he just gets on her nerves and the only reason Liz is still hanging out with him is because Sean's having so much fun with Tippy! Liz can't believe she's so petty. Before Sean can admit to the same indiscretion, Liz interrupts and apologizes for being such a terrible person. I mean, who actually fakes a friendship to stick it to their true friend? Sean's eyes widen and he shuts his mouth. Suddenly, Tippy walks in and suggests the three of them go out for drinks after work. Sean is mortified, but the date is set!
Later, Ellie finds Liz at the office and begs her to come back into Sean's life. Tippy is the absolute worst and Sean despises her. Liz can't believe it... Sean befriended Tippy out of revenge! Emboldened, Liz surprises Sean at dinner with Justin Timberlake tickets, but after he gleefully accepts, Liz says she can't go and gives her ticket to Tippy. The color in Sean's face disappears. Tippy is excited because she gets to spend the night with Sean, and even though he's gay, Tippy thinks she still has a chance. When Tippy goes to the bathroom, Sean begs Liz to save her. He apologizes for faking the friendship to get back at Liz and tells her she's the only woman he wants in his life. Sean and Liz hug it out and end their fight.
Max and Hunter show up to the bar in their chain-link slacks and are immediately ridiculed by two guys at the bar. Max realizes he sucks at trendsetting, but Hunter cheers him up by telling Max to stop trying to beat Sean at what Sean does best. Max needs to be the boss and do what "Max does best." Later, when Liz comes back over to Sean's house, Lorna excitedly runs down the stairs hoping to see Tippy. When Lorna realizes Liz is back and Tippy's gone, she offers some false affirmations before admitting she's devastated and leaving. Some things never change!