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Michael is introduced as an incompetent and unlikable boss
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The new and improved Michael Scott is introduced. He is now a goofy and socially unaware, yet competent boss
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Michael and Jan hook up for the first time
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Michael and Jan start officially dating after their trip to Jamaica
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Jan after being fired from Dunder Mifflin moves in with Michael in Scranton and uses his journal as evidence for her lawsuit against Dunder Mifflin. Resulting in a rift between them
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Michael and Jan invite Jim and Pam along with others to their house and the secrets of their awful relationship are finally revealed. They have a big fight and break up
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Michael and Holly start dating after Michael finds out Jan’s baby was conceived with donated sperm
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Michael and Holly’s relationship gets discovered by David Wallace who transfers Holly to Nashua
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Michael and Jim become Co-Managers and their styles clash. Michael enters a couple of relationships but none of them compare to Holly
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Michael decides to move with Holly to Boulder, Colorado after they find out Holly’s father is sick. He later marries her and they have children.