I've been re-watching the show on Hulu for a few weeks and I'm up to the middle of season 4.
I have to voice my dislike of Winnie Cooper. I watched the show when I was kid during its original run, and I was a Kevin/Winnie shipper and looked forward to the episodes that focused on them. I disliked every girl that turned Kevin's head or showed interest in him (Madeline, Susan, Linda, Teri, etc.). I remember I adored Winnie, loved her wardrobe, and her beautiful long shiny hair.
Now, ugh, I can't stand her and her wishy-washy treatment of Kevin. She strung him along until someone better along, and then acted hurt when Kevin said he didn't want to be friends. How oblivious (or self-centered?) could she be? She should not have been dating at the age of 12; she was clearly immature and messed up from her brother's death. I hate the annoying way she said "Hi" and "Can we talk" and "I don't know", and the manipulative way she always teared up when arguing with Kevin over their toxic relationship.
Like I said, I'm up to season 4 on my re-watch, and all I can think of when Kevin & Winnie have relationship problems is that they were too young & immature to be so obsessed with each other and should never have been allowed to date each other. How did Kevin's parents never realize how messed up their kid was because of his relationship with Winnie? Why were these kids so desperate to have boyfriends/girlfriends in middle school?
Anyway, besides the endless Kevin/Winnie episodes, I really am enjoying the trip down memory lane. My favorite episodes are definitely the ones that focus on the Arnold family, particularly the Jack/Kevin relationship. Wayne is still annoying but he has his moments...but that hair is still hideous. The Mr. Collins death episode still gets to me after all these years.