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.

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.