Complex sentence: Another person Hayden could not stand was the ladies' basketball coach Judy Watkins, whom Hayden often got into prank wars with, but was complicated by the fact Dauber dated her until 1995 when she confessed to an affair after returning from a coaching job in Romania.
Split into simpler sentences: Another person Hayden could not stand was the ladies' basketball coach Judy Watkins, whom Hayden often got into prank wars with. His relationship with her was complicated by the fact that Dauber dated her until 1995, when she confessed to an affair after returning from a coaching job in Romania.