EMILY: We were going to meet my girlfriends who were going to drive me back to school.
RICHARD: And you were angry with me.
EMILY: Because you wouldn’t commit to plans for the holidays.
RICHARD: Because I was going to invite you to the house to meet my parents after I proposed.
EMILY: Which I didn’t know because you gave me no indication whatsoever.
RICHARD: Anyway, you had just finished calling me a spineless jellyfish.
EMILY: And you got very annoyed, reached in your pocket, pulled out a box and said, “Here.”
RICHARD: And you opened the box, showed no emotion, slammed it close and said, “Fine.”
Richard and Emily describe the circumstances of their engagement at Yale University, which happens during a fight while sitting next to a trash can, with the engagement ring being offered and accepted in a fit of temper. It’s somehow reminiscent of screwball romantic comedies of the 1930s and ’40s.
They were both in collage at the time – when Emily says she was going back to “school”, she means her own college. They must have got engaged at the end of the year, because they were arguing about their “holiday” (ie Christmas) plans at the time. Yet they were still able to sit outside, so it can’t have been freezing or snowing – surely they would have mentioned that if it had been the case? They may have got engaged in November, before Thanksgiving – around this time of year, in fact, although neither of them mentions that the date is close.
The Annotated Gilmore Girls 