It is implied that they broke up in "The Job" but it is specifically addressed in "Fun Run"
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Karen Fillipelli who was played by Rashida Jones
Product Recall. Season 3, Episode 20.The episode actually starts with Jim impersonating Dwight.Then, vice versa at the end of the episode.
Season 3 "Business School"
Season 1 episode 4! ITS WHERE JIM AND DWIGHT FORM AN ALLIANCE AND JIM GETS DWIGHT TO HIDE IN A BOX DURING MERIDITHS BIRTHDAY PARTY!
The episode is "Product Recall" in the third season. Hope this helps!