Episode list

Chelsea telling Sarah not to forget her passport is the first indication that many of the staff get that Chelsea is organizing one of her infamous trips, this time back to Cabo San Lucas. She rents a private jet that can only hold herself and ten other passengers, those other ten chosen however Chelsea decides at any given moment. With one spot gone, Brad, Heather and Jiffy in particular do whatever they can to get on Chelsea's Cabo list. But as more and more spots get taken, the three of them get more and more desperate. Meanwhile, Stella, the infant daughter of Kit, one of the staffers, is in the office for the day since Kit had no other child care option. Chelsea and the writers try to tread lightly around Stella, not wanting to be a bad influence, but Stella may already have a mind of her own, even at her tender age. And Jiffy believes that being the office whipping boy is a sign of respect.

Chelsea accidentally tweets a photograph taken at a recent pool party of a faceless and exposed vagina. Good Catholic girl and mother Heather is mortified to see that it is her vagina, the photograph she didn't even know existed. Before the photograph is removed, it goes viral. But Heather's mortification turns to opportunity when she feels the publicity would be good for her book sales. But before she can pounce on this opportunity, the vagina is credited to Giuliana Rancic, who doesn't deny that it is her. Heather tries to take back ownership of her own vagina. Meanwhile, Chelsea prides herself on being loved by her entire staff. That's why she seems so upset that Xiao doesn't seem to like her. She's determined to find out if her perception is reality. And Chuy brings Catfish, his "little brother" - a black teen - into the office. Catfish's presence doesn't sit well with the other staffers who don't want to seem racist, but believe Catfish is responsible for the rash of recently gone missing items from the office.

After appearing as a guest on the show, Reese Witherspoon begins to hang around the Lately offices. At first, all the writers clamor to have her be their individual new BFF, which Reese seems more than willing to be to each of them. But over time, a little Reese goes a long way. The writers have to figure out a tactful way to tell Chelsea of Reese's intrusions into their working life as Chelsea, who has not been subject to Reese's intrusions, is oblivious to the situation and as such still considers Reese a close friend. Meanwhile, Lionel, one of the security guards, buys Heather's lunch for her at the food truck. This incident leads to some awkward encounters between the two as Heather tries to reciprocate, while Lionel begins to question what Heather's actions mean. And Chuy asks Brad, the Jewish MBA, for advice on how to negotiate his still active contract with Chelsea.

Heather and especially Sarah are perturbed that someone has been continually doing the number two in the women's restroom but not flushing. Sarah, who does almost anything required to find out the culprit (while Heather seemingly will do anything), figures that it is someone with anger issues, so she goes on a search for the angriest woman in the office. While Steve does his own somewhat creepy surveillance, Sarah thinks that Brad may know something more about it than he is letting on. Meanwhile, Chelsea has instituted the "Nope" board at the office, on which she hangs what she considers offending pieces of clothing that her staff wears. Among the items confiscated and posted on the board are Steve's running shoes (which results in him exposing his infected toes) and Johnny's selection of shirts, one of which he was planning on wearing to a small intimate party to which he has been invited by Chelsea to Jennifer Aniston's house. Heather hates the Nope board if only because Chelsea buys the person nice clothing in replacement, so Heather figures that fashion conscious people like her are left out in the cold. And Brad and Chris convince a nervously excited Johnny that he may have a chance of getting intimate with Jennifer at the party.

While Brad and Jiffy are working late one evening at the office, they are interrupted by the Latina cleaning lady who is doing her regular rounds. Brad in particular is annoyed by what he considers her intrusive manner, not only in the loud vacuuming, but also her loud voice while she speaks Spanish on her cell phone. As such, Brad has her fired the next day. What Brad is unaware of is that the cleaning lady, Guadalupe, is Chelsea's favorite. Brad also learns that Chelsea is planning on giving Guadalupe a gift when she starts her shift that evening because of a personal issue through which Guadalupe is going. Brad knows that he has to get Guadalupe rehired or his career working for Chelsea is on the line. Brad finds that rehiring Guadalupe isn't as easy as it was to get her fired. Meanwhile, Heather is rehearsing being a talk show host for that day whenever Chelsea will ask her to guest host the show or when she gets her own talk show. Sarah is Heather's pretend guest. Sarah treats the situation like the make-believe that it is, while Heather treats it like a real talk show, which causes some bad feelings in the office. And Chelsea's warm up comedian calls in sick. After going through the list of staff members to do the job for tonight's show, she ultimately chooses non-comedian Roy. Will Roy be able to discover his comedian mojo?

At the office, Heather breaks down in tears because of a potentially marriage ending fight with her husband, Peter. Off the cuff, Chelsea tells Heather that she can stay with her for the weekend, or for as long as it takes for her and Peter to patch things up. Heather gladly accepts. Chelsea regrets asking Heather as Heather treats her stay like one big grown-up slumber party. Heather's actions also start to annoy Chelsea so much that she needs to invite Sarah over to act as a buffer. Chelsea does whatever she needs to to get Peter and Heather back together. Meanwhile, Chris and Brad are performing on a double bill, the marketing which irks Brad. Sarah has invited her most ardent fan, a seventeen year old Sacramento girl named Kelly, to a taping of the show. She begins to have mixed feelings about doing so. Regardless, Steve is the one who tries to benefit from Kelly's visit. And a faceless person is caught on the security camera peeing in the studio parking lot. If it's a staff person, he could get fired. Jiffy admits to Chris, Brad and Chuy that it was him. On advice from Chris, Jiffy confesses to security, which could mean the end of his job. Chelsea goes to extreme lengths to fight corporate so that Jiffy can keep his job.

Based on what he sees as Chris' unusual behavior of late, Jiffy believes that Chris has becomes a drug addict. Although initially unbelieving of this assertion, Heather too comes to believe the same. Sarah, who believes she knows Chris the best among the staff, doesn't think there is any way Chris could be a drug addict. Regardless, they bring in some high powered help to stage an intervention for Chris. Based on what happens at the intervention, they perhaps should have staged the intervention for another staff member. Meanwhile, Roy is feeling unappreciated by the Lately staff, including by Chelsea. He states he has received a job offer to be Tori Spelling's personal chef, which Chelsea believes is only Tori's way of getting back at her for slagging her so often on the show. Roy, who is considering taking the job, will soon find out what Tori's motivations are for offering him the job. And on the advice of his agent, Chuy decides to participate in an actors' workshop to expand his horizons. Those that attend the workshop's stage presentation are surprised by Chuy's performance in more ways than one.

Chelsea takes great pride in celebrating the birthday of every one of her staff with great fanfare and festivity. So Chelsea is angry when on the next birthday in which she places Sarah in charge of getting the birthday cake, Sarah ends up getting a poor substitute for a cake: crudités. While berating Sarah publicly at every opportunity for this gaffe, Chelsea does whatever she can to make it up to the birthday boy, Micah, especially as this birthday was his first as a staffer. However, Chelsea's efforts may be more geared toward her want to celebrate a birthday her way than what Micah may want. Meanwhile, Chelsea learns that Brad has been invited to Ross and Salvador's house for Sunday brunch, Brad believing that it is a business lunch of some sort. Chelsea decides to pull one of her email pranks by sending Ross an email from Brad's email account stating that he wants advice on his own coming out. And Chuy asks Heather to emcee his foundation's fund-raiser. Chelsea tries to get out of going if only to avoid watching Heather's shameless self-promotion.