Jessica informs Stuart and Wade of her girls' night out plan to go to a gay club. Stuart invites himself along, and Jessica allows it once he offers to give up his WiFi password. He rushes to get ready, leaving Wade to watch movies alone.
Jessica greets her friends at the club, including her frenemy Amelia. Their small talk is interrupted when Amelia spots Margot, a chic tastemaker renowned for her sophisticated dinner parties. Knowing that Jessica isn't on Margot's email invite, Amelia inquires about her upcoming party on Saturday. Jessica promises she'll be there, and hunts down Margot for an invitation.
Stuart's presence at the gay club confuses both the women and gay men. He starts conversing with two gay men named Andy and Justin when he notices them talking to a group of beautiful women. Stuart learns that Andy, who runs a modeling agency, will be at Margot's party.
On Saturday, Wade arrives at Stuart's house for a movie night. Stuart ditches him once again, this time to attend Margot's party with Jessica. Left alone, Wade invites over Kives, who decides to teach Stuart a lesson. They mess around with Stuart's things and snoop through his computer. Kives finds a file called "Stuart Pritchard's Hopes and Dreams," which includes "Learn saxophone to a superb level" and "Have a threesome. Me plus two women." The boys' laughter turns serious when the list reveals that Stuart hopes to have a family. The last item reads, "Don't die alone."
Jessica and Stuart arrive at the party and greet Andy and his boyfriend Armand. Stuart is giving an awkward toast, when he's interrupted by the arrival of Justin. Noticing how well Justin's dirty jokes play to the crowd, Stuart retreats to the bathroom to search for "outrageous jokes" online. Over dinner, Amelia and Jessica learn that Armand writes a column on up-and-coming actresses for Vanity Fair. Both women tout their résumés, hoping to impress him.
As dinner breaks up for coffee, Stuart and Jessica make a pact: she'll prompt him to tell jokes and he'll compliment her acting. Their plans go over with mild success and Andy agrees to set Stuart up with a model. He asks about the woman on a Hollywood Boulevard billboard. Justin not only knows Kimberly, he invites her to the party.
Amelia reveals she starred in 'West Side Story,' and to the delight of a group, she performs a song. Not be outdone, Jessica offers to tap dance. She tapes quarters to the bottom of her shoes and performs an excruciating routine. "That was really brave," Amelia declares.
Realizing she's made a poor impression, Jessica begs Stuart to ask the group to their place where she can redeem herself. They accept his invitation. Overconfident, Stuart attempts to top Justin's jokes. He makes a gay joke with an offensive slur, and the mood chills instantly. Margot tells him and Jessica to leave. As they exit, Kimberly and her model friends walk in and climb into the hot tub in their underwear.