Ep 11. Booze Cruise

In The Office season 2 episode 11, titled "Booze Cruise," the Dunder Mifflin Scranton team embarks on a "fun" boat trip planned by Michael. As they set sail, tensions rise and secrets are revealed.

Michael sees the boat trip as an opportunity to boost morale and facilitate team building exercises. However, as soon as they set sail, things start to go awry. Dwight is convinced that someone will get left behind, leading him to go to ridiculous lengths to make sure everyone is accounted for. Jim and Katy are enjoying each other's company, but things get complicated when Roy shows up.

Meanwhile, Michael and Jan's relationship takes a drastic turn when they both get drunk and start to air their grievances. Jan internalizes Michael's lack of ambition and professionalism while Michael is upset with the way he perceives Jan as always trying to control him. Throughout the episode, the two of them continue to argue and make up, creating an uncomfortable and awkward atmosphere for everyone else on the boat.

As the boat reaches the point of no return, the tensions come to a head. The boat hits rough waters, leading to one of the most memorable moments in the series. In a now-iconic scene, Michael, in a drunken stupor, begins singing an off-key rendition of "Goodbye, My Lover" by James Blunt. The rest of the group initially groans in annoyance, but soon everyone joins in and the moment becomes a bonding experience.

Overall, "Booze Cruise" is a standout episode from The Office's second season. It highlights the characters' flaws and insecurities, while also providing some genuine moments of hilarity and heartwarming camaraderie. The episode has become a fan favorite and remains one of the most memorable episodes of the series.