Event Year: 2005

Michael had made it a point to have Movie Monday every week. He called the office into the conference room to watch a 30-minute installment of Varsity Blues, but Jan made an unexpected visit and did not like what she saw.

Kelly set Pam up on her first date since breaking up with Roy. She was very nervous. Michael tried giving her dating tips and told her she should freak her date out by wearing her wedding dress.

When Michael unintentionally outs a gay employee, he stumbles through a sensitivity mine-field. Also, we find out what happened with Jim and Pam.

In the season finale, Dunder-Mifflin holds a Casino Night in the warehouse to benefit charity. While Michael faces the task of juggling two dates, Jim is forced to ponder the reality of transferring to the Stamford branch and what that means for his relationship with Pam.