Revealing mistake: In the scene near the beginning where Leela tells Fry and Bender to watch the political debate on television, both of them (Fry and Bender) fall asleep. When Leela "hops" on the couch to wake them up, Bender's arm, despite being behind Leela, can be seen through her white shirt for a few frames.
Continuity mistake: In the Hall of Presidents, Bill Clinton's head is above Jesse Ventura and Jimmy Carter. When he starts to hit on Leela, he's now sitting above Gerald Ford. Later he shifts again, being above Carter and Ford.
Xmas Story - S2-E8
Continuity mistake: When Bender goes off the cliff, we see in the overhead shot that there are no kids on the icy lake, nor are there any tress near the lake. When it cuts there are kids on the ice and trees surrounding it. (00:02:45)
Xmas Story - S2-E8
Continuity mistake: When Fry looks up at the clock tower the display reads "04:26" which implies it is 4 in the morning, instead of before sunset. In addition, once he has climbed up to the top of the tower, the clock has no 0 before the time and simply reads "4:26". The zero returns right at the end of the episode, in a wide shot of New New York. (00:12:40)
Xmas Story - S2-E8
Continuity mistake: While Fry is commenting on it being his first Christmas without his family, it can be seen that the door to the hallway is open. but when Hermes comes in, there's the sound of the door opening. Also, Hermes waves the two stacks of cards. The stack in his right hand has a red envelope in it that changes to white in the wide shot.
Xmas Story - S2-E8
Continuity mistake: When Bender starts serving the bird for everyone, you see a chair between Fry and Tinny Tim. In the closer shot, Bender is in between Fry and Tinny Tim where the chair should be.
Why Must I Be a Crustacean in Love - S2-E9
Continuity mistake: Leela's nose disappears when Zoidberg shoves her into his armpit. (00:09:40)
Why Must I Be a Crustacean in Love - S2-E9
Continuity mistake: When Fry and Zoidberg are fighting, Zoidberg slashes the "Z" insignia (a tip of the hat to Zorro) onto Fry's shirt, then adds a D and R. When Fry releases Zoidberg from the nutcrackers and addresses the king, his shirt is repaired. (00:18:15 - 00:19:15)
Why Must I Be a Crustacean in Love - S2-E9
Continuity mistake: As Zoidberg looks around at the beach, he is suddenly up on his mound, and two females are suddenly in the scene without walking onto frame.
Put Your Head on My Shoulder - S2-E10
Continuity mistake: In the scene after Fry and Amy has been rescued it shows Hermes writing on a board. The size of the board changes in the next shot, as well as the writing on the board. (00:07:10)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Fry and Amy are kissing inside the closet the items on the shelf behind them change between the shots. This also happens later when they are breaking up in the closet. (00:07:10 - 00:13:30)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Fry says "I'm not a one woman man" to Leela while she is drilling on the ship, her grip on the drill change between the shots. (00:10:15)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Zoidberg examines Fry's body the professor is holding on to Fry's hand. When it cuts he's no longer holding it. (00:13:00)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Leela arrives at Bender's she grabs the "Dating Consulting" sign. In some shots it's not visible but in some shots it's right in front of her on the table. (00:14:20)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Fry and Amy are getting ready for their dates we see Fry adjusting the bra while Amy has her arm down. When it cuts it's up. (00:15:20)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When the door bell rings and Amy says "Come on in Gary" we can see there is nothing on the wall behind her. When it cuts a panel with three buttons suddenly appear. (00:15:40)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: At Fry and Amy's date Fry has a bite from his burger, puts it on the plate and holds on to it. When it cuts his hand's off it. (00:15:55)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Bender shows up with Fry's date, Amy's date is not sitting at the table. Two shots later he suddenly reappear. (00:16:10)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: When Bender says "She's well travelled" about Fry's date, Fry is leaning his arm on the table. When it cuts it's off the table. (00:16:20)
Put Your Head on My Shoulder - S2-E10
Continuity mistake: After the accident when Fry looks at his body, there is a tool kit or something similar more or less right in between the body's legs. In a few moments there is a shot from above and the kit is several feet to the right of the body without anyone touching it.
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]