Why did Michael break up with Jan?
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Similarly one may ask, why did Jan and Michael break up the first time?
Jan and Michael didn't officially become a couple until their hookup went public following their trip together to Jamaica. By the end of The Office season 3, Jan was fired from Dunder Mifflin so she moved in with Michael at the start of the following season. They then break up for good but that's not the end of Jan.
One may also ask, what's wrong with Jan Levinson? She's dating an egotistical, narcissistic child in Michael and she has to make peace with that consciously and subconsciously and this ends up creating a vicious cycle of psychological issues for her. She gets worse and worse because he's such a mental mine field.
Consequently, why was Jan fired from Dunder Mifflin?
Jan was fired from her management position at the paper supply company Dunder Mifflin after a year of erratic behavior, improprieties and an impulsive breast augmentation.
What episode does Michael get back with Jan?