Michael starts a romance with his boss Jan Levinson in the early seasons of The Office.
Jan is the vice president of Northeast Sales for Dunder Mifflin and initially supervises Michael, the regional manager of the Scranton branch. Their relationship begins after a business meeting at a Chili's restaurant in the second-season episode "The Client." Michael and Jan share a kiss, then gradually move into an awkward, volatile relationship.
Their romance becomes one of the show's most uncomfortable storylines because Jan often treats Michael dismissively, while Michael is eager to turn their connection into a serious love story. After Jan loses her corporate position, she moves into Michael's condominium, but their relationship eventually collapses during the infamous Season 4 episode "Dinner Party."
Viewers sometimes confuse Jan with Holly Flax, who becomes Michael's most important long-term partner later in the series. Carol Stills and several other women also date Michael, but Jan is the boss involved in his early workplace romance.