In late 1989, Jake became very close with Donna when he was just divorced from Marley Hudson and Michael had apparently left Donna. Their budding closeness led to a passionate kiss on New Year's Eve of 1990.

Freeze FrameDonna was horrified at what was developing. She and Jake had always hated each other, primarily because Donna had always disapproved of his relationship with Marley. But in early 1990 they had become quite close, and ended up spending one night together in February. Later that same night, Michael returned to her, and Donna broke off her relationship with Jake for good.

Donna greatly regrets her affair with Jake because it ended up destroying her marriage to Michael.