Michael tells everyone that they are engaged upon his return, but later admits this is not true.
When Michael comes to Nashua with Pam Beesly to give his lecture and find closure with Holly, she is not there because she is on an HR retreat.
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.
Executive producer Greg Daniels has repeatedly stated that the inspiration for Flax's character stems from a shopgirl who served him on a vacation in Newfoundland, Canada, whom he described as "a female Michael Scott." She is originally from Des Moines, Iowa, and her parents now live in Boulder, Colorado and her father suffers from dementia.
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.
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.
Holly and Michael date, and on their third date have sex in the office (inadvertently leading to the break-in at the office).
During an attempt to put a raccoon in Holly's car, a Toyota Camry Solara convertible, Dwight is berated by Michael, who takes Holly's side and loudly proclaims that she is the "best thing that has happened to him and the company since World War II." Holly invites Michael to go out for dessert after Toby's going away party, but Michael turns her down, opting instead to go with Jan Levinson, who is pregnant and had asked Michael to be there as if he were the child's father.
Michael had been courting Holly in the first episode of the season.
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.