EMILY: Everyone’s awfully quiet tonight.
LORELAI: Sorry Mom, I’m just tired.
RORY: Me too – school.
LORELAI: Dig it, man.
RORY: Peace out, Humphrey.
The audience knows why Lorelai and Rory are so quiet. Rory is depressed about breaking up with her boyfriend Dean, and Lorelai’s relationship with Max has hit an impasse: they reunited and both love each other, but the problems that ended their relationship are still there with no solutions in sight.
Lorelai says, “Dig it, man”, which is hippie slang from the 1960s meaning, “Get it, understand it, know it”. The hippies might have added the “man”, but “dig it” goes back at least to the 1930s as African-American slang, and even in the 19th century Americans spoke about “digging” in the sense of knowing or studying something.
Rory responds in a similarly counter-culture way by saying “Peace out, Humphrey”. “Peace out” is hippie slang meaning “Goodbye, go in peace”, influenced by the radio sign-off, “Over and out”.
Rory is possibly referring to Hubert Humphrey (1911-1978) who was the Vice President under President Lyndon Johnson from 1965 to 1969. The main author of the Civil Rights Act of 1964, he introduced the initiative of the Peace Corps and the National Peace Agency. Sceptical of the war in Vietnam, he was forced to support it in loyalty to Johnson. He was the Democratic nominee in the 1968 presidential election but lost to Richard Nixon – you could say that he “peaced out”.