Had this exact same experience. Picked the Simpsons just to try it out and in the first pair up was S1 stuff vs some episode from S18 I've never seen. So I pic

Had this exact same experience. Picked the Simpsons just to try it out and in the first pair up was S1 stuff vs some episode from S18 I've never seen. So I picked The S1 episode. Then it was another S1 episode. Repeat. Then an S2 episode. My second option never changed from that first episode from S18 so I never picked it. Perhaps I could have gone through 12-17 seasons of episodes always picking option one until two episodes I've never seen went head to head. IMO, both options need to randomize each time until first pairings are exhausted.