Season 1, Episode 6: "Hot Girl"
In case you ever feel like you're terrible at flirting, this is a great episode to put things in perspective. Michael Scott's awkwardness is taken to the next level when he's in the presence of a woman he fancies and when that woman happens to be Katy, an attractive handbag seller played by Amy Adams. Prepare to cringe like you've never cringed before. Right off the bat, Michael demonstrates his extreme lack of self-awareness by referring to her as "the new-and-improved Pam" . . . in front of Pam, which sets us up pretty nicely for the escalating discomfort that ensues. This episode also reveals the flip side of Michael's less-than-stellar flirting, which is that he's really just a romantic at heart. He spends the episode earnestly trying to woo Katy, and when she agrees to let him give her a ride home at the end of the day, he enlists Ryan to clean out his car and basically excitedly counts down the seconds until 5 p.m.