At one point, after transferring to a new school, she starts giving Kevin the cold shoulder, out of guilt, because she met someone. She felt bad, but just kinda strung him along until she couldn’t take it anymore.

They get back together and Kevin did blow it when he insinuated to his friends that he and Winnie slept together, but within a week or so, she’s hanging around another guy. Granted, I don’t think they were serious, but for a girl that had a reputation so to speak, that didn’t look so good and she bounced back FAST.

And then, after about six and a half years together, she’s embarrassed to be seen with him in his car, teases a special Christmas gift and gets him a record of a band he doesn’t even like.

Cool...

She messed with his head throughout the entire series IMHO.

Although Kevin was pretty unlikable in the later seasons she still treated him a bit off at times. Winnie was just too hot and cold for my liking.

Most teenagers are not likeable in real life that is what made this show fun to watch, kevin was kinda needy had options of dating taller and more popular boys, kevin was just a average guy who barely had girls interested in dating him due to him not being popular

Kevin was probably just as much troublesome.

I dont think kevin was that bad lol he was needy he kept chasing winnie even tho she never liked him lol