Which popular eighth-grader does Winnie date early in The Wonder Years?

Winnie dates popular eighth-grader Kirk McCray early in The Wonder Years. Their relationship appears after Kevin meets Winnie in the pilot, creating the first major romantic obstacle between the two eventual central characters.

Kevin’s feelings for Winnie remain unresolved while she is with Kirk. At the same time, Kevin briefly dates Becky Slater, partly because he is trying to cope with Winnie’s relationship and partly because adolescent romance on the show is driven by jealousy, uncertainty, and social status.

Winnie eventually ends her relationship with Kirk, and Kevin and Winnie share a second kiss at the beginning of the summer of 1969. Kirk is therefore an important early rival, but not Winnie’s lasting partner or the show’s principal romantic storyline.