I'm trying to think of an old episode of a show. The plot is similar to the Gidget episode with Richard Dreyfuss - a young girl takes pity on an awkward boy, and goes out with him to raise his confidence. She decides he has a crush on her, and so decides to let him down easy.

The twist here is that the boy tells her that he's glad he dated a "nice girl," but now he'd like to date some "rotten girls." I think the boy might be lanky blonde kid who was in a lot of shows in the 1960s. There's a Patty Duke episode that seems to use this story line, but if so I'm thinking of the wrong kid.

Again, "rotten girls."

I don't think this is the one you have in mind, but Father Knows Best did have an episode with Betty (Elinor Donahue) and a very awkward guy -- Betty's friends if I recall correctly set her up with him as a joke. If it's the ep I'm thinking of, he's working in the ice cream parlor (and turns out to be a star football player).

I believe it was from one of the later seasons, maybe from one of the last 2 or so.

The "rotten girls" thing may have applied to that ep, or there might've been another with Betty -- where at the end, the guy wants to try other dating (after being attracted to Betty the whole time).

I think it might be The Partridge Family with Laurie but I'm not sure.