While eating at Petite Abeille, Whitney and Jay talk about his band's upcoming gig at New York City venue Cutting Room. Whitney's invited Erin and Olivia to see the Tamarama show. Jay jokingly tells Whitney that he'll corner off a little area for Olivia so she doesn't have to "mingle with the commoners."
Meanwhile, on the Upper East Side, Olivia meets Nevan for lunch at La Goulue. After reprimanding Nevan, for calling her "babe," Olivia tells him that Whitney has invited her to see Jay's band play. Olivia doesn't know anything about Tamarama, so Nevan advises that she remember to smile and clap.
The night of Tamarama's Cutting Room gig, Whitney and Erin hail a cab and head to Olivia's apartment in Tribeca. On the way, Erin tells Whitney that her ex-boyfriend JR may be coming tonight. She goes on to say that she's told JR about Duncan and hopes that JR doesn't ask her to get back together. When Whitney asks Erin whether she wants him back, Erin says only that the timing is bad.
Olivia fluffs pillows in preparation for Erin and Whitney's arrival while her dog, Mr. Butler observes. When Whitney and Erin arrive, they immediately marvel at her closet and how pretty the apartment looks. Like any good hostess, Olivia offers her guests "champy" (a.k.a. champagne), but Whitney says they're in a bit of rush. Olivia isn't worried and tells Whitney that Jay wouldn't start without her being there.
Over at the Cutting Room, Jay and his Tamarama bandmates are setting up for their gig. Adam shows up and asks Jay whether Whitney has arrived. Jay replies, "She'll be here -- she better be here."
Back at the apartment, Olivia is pouring the champagne. Mid-pour, Olivia decides that she should be wearing all black for a rock concert. Whitney and Erin try to convince her to stick with the current outfit, but Olivia has already headed to the closet to find something else to wear. Erin and Whitney exchange concerned glances and Erin mouths, "we've got to go!"
At the Cutting Room, Jay and bandmate Pottsy decide they have to start the show -- with or without Whitney. Samantha and Adam watch from the crowd as Tamarama's music fills the room. Still no Whitney.
Whitney calls to Olivia, who's still in her closet finalizing her outfit, telling her that it's time to go. Olivia says that she's "totally ready" and rejoins the girls in the living room to find Whitney holding a man's sock that she's pulled from the couch cushions. Whitney asks whether the sock belongs to Nevan. After a resounding "Eww!" the girls head out.
It's standing-room-only as Whitney, Erin and Olivia make their way through the crowd at the Cutting Room. They settle on a spot in the front of the crowd to watch Jay's band perform. Olivia feels bad as she accidentally bumps into neighboring concert goers. Erin tells her it's "a concert, honey -- you bump all you want!" It's not long before JR arrives, and although Erin seems happy to see him, she tells Samantha that the situation is reading 9.5 on the awkward scale.
When the band takes a break, Jay immediately heads into the crowd to find Whitney. Jay tells Whitney that she made it just in time. Olivia joins them and says goodbye -- she has to work in the morning. After Olivia makes her exit, Erin and Whitney head to the bathroom hallway where Whitney tells Erin that Jay's bandmates were giving her a hard time for being late. Whitney feels horrible but Erin reassures her that it wasn't her fault. Jay finds the girls in the hallway and Erin apologizes to him for being late. Jay suggests that they just forget about it.
The next day at the Diane von Furstenburg offices, Whitney asks Olivia if she enjoyed herself at the Tamarama show. Olivia says she did. Whitney then tells Olivia that she felt badly for showing up late. Olivia dismisses Whitney's comment, saying that it's "not the end of the world" because she's got something better lined up for Tamarama. Olivia tells Whitney that her friend needs a band to play an upcoming charity event, so, she suggested that Tamarama play the event. Surprise! Whitney tells Olivia that it'll mean a lot to Jay.
While lounging on Whitney's couch, Whitney tells Jay about Olivia lining up his band to play at an upcoming charity event. Jay jokingly asks whether Olivia is his booking agent, but then tells Whitney he'll give it a shot.
Erin greets JR on the street outside of Antique Garage before heading inside for dinner. Once they're seated, JR tells her that despite all that has happened since they were together he feels that they've picked right back up and he can't stop smiling about it. Erin laughs and tells him that his timing is really bad. JR agrees, but says that this is still where his heart is. It may be that JR knows where his heart lies, but Erin doesn't seem so sure.
Later at Erin's apartment, Whitney asks Erin and Samantha about their plans for the night. Erin tells them that JR is bartending at Brother Jimmy's if they want to stop by, spawning a conversation about Erin's relationship Duncan and JR's re-entry into her life. Erin says that Duncan's been perfect and so supportive. Whitney thinks that Erin might as well have fun tonight and get some free drinks out of it.
When Whitney and Olivia arrive at Hotel Gansevoort for the Completely Bare Charity Event, Tamarama is already setting up on the stage. The band starts to play as Olivia and Whitney greet other guests and find Nevan in the crowd. Olivia suggests that the three of them find a seat but Whitney decides to remain standing so she can see the band.
Meanwhile at Brother Jimmy's, Erin and Samantha arrive and greet JR who's stationed behind the bar. Erin turns to Samantha and says that JR is "so cute," she wishes that she didn't have a boyfriend right now.
Back at Hotel Gansevoort, Nevan begins making jokes about the band to Olivia and Teresa, the event planner. Gesturing in the direction of the band, he says that it's a "glossy high end place" but it's like the "beach boys" over there. The jokes continue even as Jay gets off stage to find Whitney. Jay wants to leave immediately and asks Whitney to keep "Bevan" away from him. Olivia notices the hasty departure and comments to Teresa that it was disrespectful of Jay to leave without saying goodbye. Nevan remarks, "What do you expect from the plaid mafia?"
While on a break from bartending, JR, who knows Erin well enough to know something is bothering her, asks her what's wrong. At Erin's request, they step outside of Brother Jimmy's to continue the conversation. She begins to tear up as she explains to JR how confused she is, telling him that she doesn't know what she wants right now. JR asks whether they're still going to hang out. After a long pause, Erin tells him she doesn't know. JR wipes away her tears and they hug.
The following day at DVF, Olivia asks Whitney what she thought about last night. Whitney thoughtfully repeats the question and tells Olivia that it was kind of like a stab in the back to have Nevan making fun of the band the whole night. Olivia says that Nevan is an adult and she has no control over him, all that Olivia asked for was a thank you. Whitney explains that Jay didn't feel like he owed anyone anything when it seemed like Olivia could have cared less. Olivia points the blame on Jay's insecurities and cuts the conversation short by telling Whitney that this is neither the time nor the place for this discussion. In the future, Olivia notes, they should leave their work environment separate from their private affairs.