RORY: You like piña coladas.
LORELAI: And getting lost in the rain.
A piña colada is a cocktail made with rum, pineapple juice, and coconut milk or cream, served either blended or shaken with ice. It may be garnished with a pineapple wedge, a maraschino cherry, or both. The cocktail originated in Puerto Rico, is its national drink, and its name means “strained pineapple” in Spanish. One story is that the cocktail was invented by Puerto Rican pirate, Roberto Confresi in the 19th century; the less exciting but more probable version is that it was invented in 1954 at the Caribe Hilton Hotel in Puerto Rico by bartender Ramón “Monchito” Marrero.
Lorelai refers to “Escape (The Piña Colada Song)”, written and recorded by British-American singer Rupert Holmes, released as a single from his 1979 album Partners in Crime. The song is about a man who is bored with his current relationship, and answers a lonely hearts advertisement in the newspaper which begins, “If you like piña coladas …”. When he meets up with the lady, it turns out to be his partner, who was equally bored in their relationship. They realise they had more in common than they realised, and their relationship is now reinvigorated. It was an international hit, and went to #1 in the US and Canada. Ironically, Rupert Holmes has never drunk a piña colada, and the original lyrics were, “If you like Humphrey Bogart”.
Lorelai gets the words slightly wrong. The lyrics are actually:
If you like piña coladas
And getting caught in the rain
not getting lost in the rain.
The Annotated Gilmore Girls 