The reason why Pen15 works and this doesn't, is simple. The creators drew from their personal experience as teenage girls in the early 2000's. To create and star in a show about teenage girls in the early 2000's.
Chad's creator appears to have drawn what she remembers what teenage boys in the mid 90's. To create a show about a teenage boy that takes place today.
I know because I was a teenage boy in the early 90's and now have a teenage son.
Oh and if your wondering why a grown man is watching Pen15. It's because I also have a teenage daughter who loves that show. So I watched a few episodes with her.