The Wonder Years

Season 3 Episode 13:

She, My Friend and I

Paul and his girlfriend Carla have a falling out. Wanting to make his friend feel better, Kevin offers to set Paul up with Winnie. At first Kevin is happy about the idea, but after awhile, he begins to wonder if he's made a mistake.
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About The Wonder Years:

Kevin Arnold recalls growing up during the late 60s and early 70s; the turbulent social times make the transition from child to adult unusually interesting.