Sherry is the ex-fiancé of Christopher Hayden and mother of Gigi. She comes across as extremely into planning and organising, which permeates her world right down to her appearance and, of course, her relationship with Christopher. This characteristic can lead her to be blunt when she wants something, like spending time with Rory. She works in sales for L'Ôreal and is referred to as being quite successful at her job, which she later has a hard time letting go off, moreso out of her need to cling to planning her life to a T.
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, and she and Christopher split up. In 2006, 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 to see her mother again.
- 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.
- She used to work for L'ôréal.
- Presenting Lorelai Gilmore • I Can't Get Started • Norman Mailer, I'm Pregnant! • Bridesmaids Revisited • The Great Stink • French Twist