If you loved Clueless, try I Could Never Be Your Woman
A bridge between a film you've already seen and one most people haven't. I Could Never Be Your Woman has roughly 10.5× fewer votes than Clueless — it's a deeper cut, not a mainstream recommendation. Here's what they share, and what the second one does that the first one doesn't.
What they share
Both films are directed by Amy Heckerling, and they sit in Comedy / Romance territory. If that's the register that drew you to Clueless, the second film will land in a comparable space — through a different lens.
What I Could Never Be Your Woman is
Amy Heckerling’s rom-com gently judges how young love and old(er) love collide. A single mom’s new flame is 24 years her junior, complicating both their lives. The film settles for agreeable without ever being sharp.

