It’s been several years since I graduated from college, so I’m unqualified to say with certainty whether or not it’s a regular occurrence for today’s savvy students to bond over their love of Ashlee Simpson, whose last album came out before some of them were born.

This unexpected celebration of the “Pieces of Me” auteur is one of several moments in Benito Skinner’s new Amazon comedy Overcompensating that feel not exactly “wrong,” but more appropriate for juvenile millennials than Zoomers. Almost every pop culture reference in Overcompensating, including extended nods to Twilight, Glee and the reappropriated Megan Fox classic Jennifer’s Body, comes across, at best, as a thing that the main characters might have discovered from their much older siblings. Or parents.

It all fits because the cast of Overcompensating projects, top to bottom, as several years older than the characters they’re playing, a...