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Michael initially dislikes her because she is part of Human Resources, but quickly falls in love with her.She is subjected to hazing by Dwight Schrute, who convinces her that Kevin Malone is mentally challenged, a belief she continued to harbor until Season Five when it was embarrassingly pointed out to her that he wasn't.This, in addition to feeling no connection with Jan's baby, prompts Michael to apologetically hug Holly and ask her out on a date, which she accepts, visibly moved.
In her early life, she held the position of hall monitor in middle school due to her geeky demeanor, and because of this, was a target of harassment by other students.
It is also revealed that she is dating one of the salesmen there, A. David Wallace lets Holly and Michael do a skit about the history of Dunder Mifflin; the two decide to do a skit that spoofs Slumdog Millionaire.
J., which deeply upsets Michael and makes him unable to do his presentation; he ultimately breaks down and asks her boyfriend about Holly in front of everyone before leaving. The presentation goes horribly and gets worse when they reveal that the Buffalo branch is closing down, much to everyone's surprise.
He tells Pam about it, and Pam volunteers to read it herself and deletes it afterward, telling Michael it said she still has feelings for him and that it isn't over. Holly and Michael reunite at the Dunder Mifflin company picnic for the first time since she was transferred. Her return is hinted at in the season finale, "Whistleblower," after Michael takes the fall for Sabre's defective printers.
In return for his loyalty, Michael requests that Holly be returned to Scranton. Holly first appears over speakerphone in "Sex Ed", when Michael calls her in fear that he may have contracted herpes and infected Holly with it.