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Heddy moves into Herman's apartment building in the third season, and shortly thereafter, the two actually admit to romantic feelings, and begin to date. Keeping true to her character, however, Heddy soon breaks up with Herman, citing that his financial prospects are not up to her standards.
- Sitcom
While working late to finish a project, Herman eavesdrops on Heddy and her date. After finding out he is married, Heddy turns to Herman for solace. They eventually wind up sleeping together in Bracken's office, but don't know how to handle the affair the next morning.
Sep 8, 1991 · Heddy winds up with Herman (William Ragsdale) after-hours in Mr. Bracken's office. Heddy: Jane Sibbett. Simon: Robin Sachs. Louise: Yeardley Smith. Mr. Bracken: Jason Bernard.
Both Louise and Heddy seem intrigued by Herman's lesbian ex, Rebecca. When Bracken consults Heddy on a gift for his wife saying that "She knows what a woman wants", Heddy's flustered reaction implies that she might have Experimented in College.
Herman is struck dumb when he tries to give a speech at a conference. Crawford: Edward Winter. Hypnotist: Susan Diol. Little Herman: Edan Gross. Louise: Yeardley Smith. Heddy: Jane Sibbett.
A Kept Herman: Directed by J.D. Lobue. With William Ragsdale, Hank Azaria, Jane Sibbett, Yeardley Smith. Herman is loaned out to Victoria Stark, a high powered editor in the company. A jealous Heddy makes waves.
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With William Ragsdale, Hank Azaria, Jane Sibbett, Yeardley Smith. Herman is working alone late at the office. He hides when Heddy brings a man back to the office and then admits he's married.
