The staff of Chelsea Lately go into chaos when Chelsea realizes she needs more people to go with her on her trip to Cabo. With all the chaos going on, Chelsea just sits back and enjoys watching all the things her staff members will do just to get a ticket. Meanwhile, one of the workers brings their child to the office, which disrupts some of the other staff members. The 'Chelsea Lately Staff Stock' is introduced in this episode.
The staff of Chelsea Lately find a naked picture of Heather on the internet, which Heather worries about until she realizes that any press is good press. That is until the blogosphere believes it is a photo of Giuliana Rancic. Chelsea tries to figure out why production crew member Xiao Niu does not acknowledge her existence despite being his boss. Meanwhile, Chuy participates in a big brother – little brother program and brings in a guy off the street named "Catfish" who steals belongings from co-workers.
Reese Witherspoon visits the Chelsea Lately offices, but the writers soon regret welcoming Reese when she starts annoying everyone. Chuy starts demanding perks from Chelsea, such as his own personal assistant. Heather feels sorry for one of the security guards when she buys him lunch, and when she tries to reciprocate, the guard refuses because he does not want to be involved in what he thinks is an affair.
Sarah and Heather try to discover who has been using the women's toilet and not flushing, disrupting their normal work schedule. Chelsea's infamous "NOPE" board is introduced, and when Steve Marmalstein receives new shoes for having them put on the NOPE board, Heather goes out of her way to get free clothing.
When Brad becomes upset at how the late-night maid Guadalupe acts on the job, he has her fired until everyone reveals that Guadalupe was Chelsea's favorite. The next day, when Chelsea reveals that she is going to stay late that day to give Guadalupe a "Get Well" gift basket because Guadalupe's son is in the hospital, Brad tries to get Guadalupe rehired.
When Heather has a fight with her husband, Chelsea invites her to stay at her house for the weekend. However, she soon regrets the invite when Heather has her cougar friends (including Vicki Gunvalson) for over a pool/Botox party. Meanwhile, Jiffy worries about the possiblity of being fired after he is caught on camera peeing in the staff parking lot.
After Sarah Colonna gets a crudité platter for staff member Micah's birthday, Chelsea becomes extremely upset because she loves birthdays and that everyone should have a cake for their birthday. Meanwhile, Chelsea has hacked into Brad's computer and sent an e-mail to Ross Matthews, claiming that "Brad" is ready to come out of the closet and needs someone to talk to. Ross (and his partner Salvador) invite Brad over to their house for brunch, which ends up an awkward mess when Brad realizes that Chelsea has pranked him. Heather is in charge of a charity event for Chuy's "Little Nugget Foundation", a drug rehabilitation program in Chuy's hometown in Mexico, and requests that Chelsea be there.
Roy considers a job offer from Tori Spelling, one of Chelsea's favorite targets on her show, after he is not being treated with respect at the Chelsea Lately offices. Jiffy and Heather stage an intervention with Doctor Drew Pinsky because they think that Chris is abusing drugs.
After Brad is rude to a fan with autism at a book signing, Jenny McCarthy tells him that he has pissed off the entire autistic community and he has to make a formal apology. Chris goes out on a date finds out that he might be a grandfather. Chelsea wants to buy Jen's friend's dog for 10 grand.
When Sarah gets a glimpse of Brad's penis while walking by as he's changing clothes in his dressing room, things go awry as she tries to prove to Chelsea that Brad's penis is the complete opposite of what Chelsea thinks his entire body is: hopelessly ugly. Meanwhile, Jiffy gets blamed when Chelsea accidentally lets an internal email (insulting Sharon Osbourne) go viral. Chelsea forces Jiffy to take the blame for her mistake, and apologize to the outraged Osbourne in person.
Brad takes Chelsea's differently-abled fan Jordan out on a night on the town to gain points with Chelsea. Heather gets jealous that the talent department takes the free gifts that companies send them to wear. Chelsea tasks Jiffy to deliver a stool sample to her doctor.
Chelsea's assistant asks the group to assemble a "Tribute Book" with photos of them and their mothers for Chelsea's birthday. Chuy invites Brad, Heather and Jiffy to an appearance at a new golf course. Chris and Jen attend Roy's photoshoot for PlayGirl.
The writers struggle to deal with an increasingly lazy and cocky production assistant. Chris feuds with James Van Der Beek over which of them will wear a matching shirt on-air. Josh is dismayed to learn that his son thinks that Chuy is funnier than Josh is.
Heather attends an office party and wakes up with an unexplained hickey; Jen becomes friends with Dave Grohl; Sarah receives a mysterious package at the office.
Reese Witherspoon returns to the Chelsea Lately offices so the writers can help her write a speech she is giving in Chelsea's honor, but she starts to bother Chelsea this time around while earning the staff's praise. Jen lies to Gary of HR to give Sarah a spot in front of the offices, leaving Brad angered that he has to use the parking garage. Roy gets upset when the writers like Chuy's salsa rather than his cooking.
Josh bets Jay Leno over the game at Ross' football party. Chelsea is the only one that enjoys her assistant's character with a lisp. Jiffy meets with Jane Fonda to discuss her coming on the show. Chelsea introduces the group to Jennifer Aniston, who has more to say behind Chelsea's back than expected.
In the season premiere, Chelsea mistakenly leaves a pile of papers lying around the office for Jiffy to find. Turns out, Jiffy has stumbled upon feedback that the network has retrieved from a focus group all about Chelsea's crew of misfits! When Jiffy shares the reviews with his coworkers, they all fight to save their jobs by changing parts of themselves that were criticized. Meanwhile, Chelsea invites the whole gang to a fundraising event which they all blindly accept. Little do they know what they're getting themselves into!
Jiffy's fellow writers believe that Hank, the studio's aging maintenance man, has a gay crush on Jiffy. Sarah doesn't like that Chris has jumped on the bandwagon to give himself a fake assistant. Chelsea enacts a specific punishment for Brad for being late to meetings. Heather uses a black doll in a baby's car seat to be able to drive to work in the carpool lane.
Heather thinks Chelsea's love life needs some spice, and Chris suggests she date someone in the "Chelsea Lately" production crew. See if Chelsea will make a love connection with crew member Andy. Plus, the staff is pranked by an unexpected masseur. Meanwhile, Brad forgets his employee badge at home--and the security guard at the Universal Studios won't let him on the lot without it, so he spends the day trying to sneak past the guard.
Chelsea asks Jiffy to work on a project ghost writing a book for her new dog, Jack. Ben Gleib comes to the conclusion that Chelsea wants to have sex with Jiffy, despite she knowing that Jiffy is married. Meanwhile, Sarah and Brad notice that one of the staff accountants has a disabled parking pass but doesn't seem to be disabled.
Kate Beckinsale insults Chelsea for her lack of physical fitness and Chelsea decides to dictate part of Kate's health regimen to her writing staff: a five day juice cleanse. Heather receives a largely inaudible angry voice message from Chelsea. Heather does whatever she can to figure out if Chelsea is indeed angry at her, or if Chelsea pocket dialed and that the screaming was directed at someone else. And someone has damaged Fortune's car in the parking lot in an apparent hit and run.
The writing staff is excited by the news that Ross will once again be hosting the show tomorrow. Chelsea does whatever she can to make her staff like her as much as they seem to like Ross. Brad and Jiffy, notice that Chelsea's dog Jackie seems to be going down on Heather. Chuy seems to be on a self-empowerment movement. He mentions that he is because of his friend "Melissa".
Sarah goes on a date with T.J. Miller, who gets physical. Chelsea offers the staff a writers retreat in Cabo, which conflicts with Heather's schedule. She bumps the other event, but comes to regret it.
Chelsea comes face-to-face with the Kardashians; Sarah and Jen get into a fight; the gang avoids the voice over guy, Mike Rock.
