CHRISTOPHER: I saw the look. Same one you had that time you ended up on homecoming court.
LORELAI: Ugh, someone’s idea of a sick, sick joke.
Homecoming is an annual tradition in US towns, high schools, and colleges, to welcome back former members of the community. It’s usually held in late September or early October, and revolves around a central event, such as a banquet or dance, following a major sporting event, often American football.
The homecoming court is a group of students chosen to represent the school, consisting of a homecoming king and queen who are senior students, and sometimes a court of royalty, escorts, princes and princesses, or dukes and duchesses, from lower grades. Lorelai didn’t do her senior year at school, so she must have been one of the younger students in the homecoming court – an experience she obviously didn’t enjoy, although it shows she was a popular student.