Via remote webcam, Andy is excited to talk to his buddies back at the office from his family boat, bound for the Caribbean. He's only been out three days, but he's already quite sunburned and haggard. He fumbles with his desalination gear and soon drops it overboard. It's not long before he does the same with his notebook computer. Guess that's the last we'll see of Andy for a while. Later that morning, the office is abuzz with a big opportunity. Wallace has called and tipped off Dwight that the Scranton White Pages is looking for a new paper supplier. Dwight's excited that David has designated him to go after "The White Whale" - the customer that the team has dreamed about for years. There's just one problem: the customer is female. Everyone knows that Dwight can't sell to women.
Recognizing Dwight's dilemma and the importance of a big new contract to the company, Pam and Phyllis step in. With Nellie, they try to smooth off some of through edges by role-playing. They tell him it's critical to really listen and make eye contact. It's hopeless. Finally, Pam's motherly instincts take over, and she decides to accompany him to the sales meeting.
Jim is on the phone with his partners in Philadelphia; the connection is awkward, and Jim still feels like he hasn't quite connected. Lack of face time looks like it might be an issue.
Angela confides in Oscar that she believes that her husband, the Senator, is having an affair. Oscar minimizes the notion to Angela. However, after finding out that the Senator is spending a lot of time at a yoga class with someone named Blake, Oscar too grows suspicious, thinking that The Senator may be cheating on him. Angela and Oscar decide to go to the yoga class to spy on him. At the studio, they find the Senator flirting with a man. Seeing Oscar suddenly grow jealous at the sight of her husband with another man, Angela starts to put some things together.
Pam and Dwight arrive at the White Pages customer's office - but they still don't know whom they're meeting. Suddenly, Jan, Michael's ex-lover and ex-boss, pops out. She's the new client, and she demands to see David Wallace. Pam and Dwight explain that they're there on behalf of David. Jan's incensed. She yells at her assistant and tries to dismiss them. Dwight pulls Pam asides and instructs her to stall while he heads off to save the sale. Pam, looking to keep the client warm, asks Jan about her daughter. Jan takes the bait, and soon the two moms are looking at a slideshow of little Astrid. Dwight returns with Clark, explaining to Jan that he is her new personal assistant - he is available to satisfy every wish she may need during the sell. Jan is captivated by the offer. She informs Dwight that he and Pam can leave and that she will be in touch. She tells Clark to stick around.