I, Roommate - S1-E3
Trivia: Bender's apartment number is 00100100 which, on the ASCII chart, is a Dollar sign. (00:05:35)
I, Roommate - S1-E3
Trivia: The title of this episode ("I, Roommate") is a parody of one of Isaac Asimov's books, entitled "I, Robot."
Answer: Yes Leela knew from early on that Fry had feelings for her. They were pretending to be a couple in 'A Flight to Remember' from season 1 and Fry tried to get on dates with Leela ever since. She just didn't show signs of the feelings maybe being mutual before some of the later episodes.
Andreas[DK]