Michael takes the entire Dunder-Mifflin staff on a motivational cruise aboard a party boat on Lake Wallenpaupack, but his planned presentation is bogged down by numerous distractions, including a dance contest, limbo, snorkel shots, and the pushy Captain Jack. Also, Jim and Katy’s relationship hits the rocks as Roy and Pam finally set a wedding date, which does more than disappoint Jim, and by the end of the night, Michael’s motivational cruise doesn’t go completely to waste when he shares a heart-to-heart with one of the workers.
Jan holds a “Women in the Workplace” seminar at Dunder-Mifflin for the paper company’s female employees. Michael, feeling more than a bit left out, decides to have his own “seminar” when he takes the male workers down to the warehouse.
Michael and Jan reveal their hushed romance while attending the Dunder Mifflin CFO party. During the party, Jim finally meets Karen's ex. Meanwhile, the rest of the office staff booze it up during happy hour.
When Phyllis gets an unexpected eyeful from a flasher. Michael decides to take the women of the office on a special outing. Meanwhile, Dwight and Andy work to track down the flasher.
Michael and Holly have sex for the first time, and Michael holds a fund-raiser for the office after it is burglarized. Dwight confides in Phyllis after Andy and Angela set a wedding date, and Jim runs into Pam’s ex-fiancé Roy.
Michael gets worried after a request from Jim, and Pam’s busy with wedding planning. Darryl’s worker’s compensation claim makes Dwight suspicious.
Michael meets with an insurance salesman that visits the office and is later convinced by Dwight and Andy that he is part of the mafia. Erin accidentally ruins Pam’s painting.
Michael, believing he has herpes, contacts all his ex-girlfriends, including Jan and Holly. Andy tries to play on Erin’s compassionate side by holding a sex education meeting for the office.
Michael tries to save Ryan's company by encouraging co-workers to invest. Meanwhile, Dwight has big plans for the office at Thanksgiving.
Traveling salesman Todd Packer comes to Dunder Mifflin looking for a desk job in the office. However, the office is unsure if they want him to work there due to his previous behavior. After dealing with computer problems, Andy confronts office administrator Pam to get a new computer.