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Sherry is the ex-fiancé of Christopher Hayden and mother of Gigi. Sherry is first mentioned when Christopher tells Lorelai that he moved to Boston to live with his girlfriend. Sherry meets Lorelai and Rory, when Christopher brings her to Rory's debate. She tells Lorelai that she really wants to bond with Rory, and she and Rory spend the next evening together. Later, Christopher visits Lorelai and Rory, and tells Lorelai that things are not working out between he and Sherry.
He and Lorelai sleep together, but when he learns that Sherry is pregnant, he goes back to her. Sherry gives birth to a daughter, Georgia, nicknamed Gigi. After two years, Sherry abandons Christopher and Gigi to take a job in Paris (5.06), and she and Christopher split up. In Season 7, after several years without contact, she gets in touch with Christopher and tells him that she wants to see Gigi again. Christopher and Lorelai accompany Gigi to Paris in 7.07.
- Although she only appears in a few episodes in Seasons 2 and 3, she is referenced throughout the series.
- Despite it being said that she wanted 2 children, when she became pregnant she mentioned thinking of abortion. She also walked out on her child to take a job in Paris.