Did kevin make it worse by chasing after winnie who was not interested in him at that point in time, there was real romantic relationship between them in season 4 ???

https://www.youtube.com/watch?v=n3eJkf4erbI
https://www.youtube.com/watch?v=n3eJkf4erbI
https://www.youtube.com/watch?v=n3eJkf4erbI

He was wasting his time chasing after a girl who had no interest