From Cher to Chaperone: Watching Clueless as a Mom in Midlife

When Clueless hit theaters in 1995, I was a teenager who worshipped Cher Horowitz. The outfits. The hair. The computerized closet. The casual confidence. I didn’t just want to be her—I wanted her life. Minus the freeway driving.

But now? I’m 42. I have a daughter who’s closer to Cher’s age than I am. And watching Clueless with her? It hit different. Like holding a mirror up to who I was—and who she’s becoming. A movie that once felt aspirational now feels like a time capsule, not just of youth, but of everything I’ve carried into motherhood.

Suddenly, I relate to Mel. I used to laugh at Cher’s grumpy but loving dad. Now? I am him. I, too, want everyone to drink water, use their head, and not date anyone with visible sideburns. Mel wasn’t cranky—he was tired. Of people’s nonsense. Respect. And while I could feel the protective love of Mel over his only daughter, I didn't understand it the way I do now. The worry, the amusement, but mostly the pride he exhibits over Cher and her antics has never been more relatable. It’s a vibe every mom of a teenage girl knows intimately.

Tai’s makeover makes me pause. When I was younger, I saw it as a fun transformation. Now, I think about how many times I’ve tried to edit myself to fit someone else’s idea of enough. Watching it with my daughter, I wondered—how do I help her trust her own voice sooner than I did? While the movie concludes with Tai finding a balance between who she was and who she became, the idea that she had to change everything about herself to fit in with Cher and Dionne went over my head when I watched it as a teen. Now I want to do everything I can to make sure my daughter always feels like enough—and if her friends ever suggest she needs a total makeover to belong, I’d be the first to say, “Find new friends.”

Josh feels way older now—and I have questions. Back then, Josh was dreamy in a brooding-college-guy way. Now, I’m like: why is a college freshman hanging around his ex-stepdad’s high school daughter? Where are his friends? Does he pay rent? And what message are we sending about who deserves our affection? Not to mention the fact that he was introduced to her even younger and in the context of an older sibling. The power imbalance inherent in their relationship is hard to ignore as a grown-up—and harder still as a mom.

Would I let my daughter date a Josh? Not without a very long conversation—and even then, maybe not. I want her to understand what respect looks like in a relationship. The kind of love that sees you for who you are—not who someone wants you to be. Watching that final scene now, I realize how rare that kind of connection is, and how worth waiting for. But let’s be honest—it still feels icky.

When I showed Clueless to my 15-year-old for the first time, she was the one who immediately flagged the Cher-and-Josh situation as problematic. I didn’t even need to say anything—she called it out herself. The age gap. The quasi-family history. The weird power dynamic. It was a reminder that today’s teens are watching with sharper, more critical eyes. And it made me both proud and a little relieved. Maybe we are doing something right.

Cher was trying. Like, really trying. For all her privilege and superficial moments, Cher genuinely wanted to do good. She cared about people. She wasn’t just popular—she was kind. And she evolved. Watching her now, I don’t just see a character. I see a girl who’s learning, falling, and getting back up. Isn’t that what we want for our daughters, too?

Fashion is still armor. Those outfits weren’t just cute—they were power moves. Sometimes putting yourself together is how you get through the day. Cher knew that. Midlife women know it, too. And honestly? So do teens. My daughter watched that plaid suit scene like it was gospel.

And then there’s Dionne. I didn’t give her enough credit back then. She was stylish, smart, and totally her own person—even when surrounded by chaos. Watching her through a midlife lens, I see how much strength it takes to stand your ground with grace. She wasn’t just Cher’s best friend—she was a whole force in her own right. I want my daughter to see that, too.

Let’s talk about those teachers. When Cher and Dionne orchestrate a teacher romance to bump up their grades, it felt funny and harmless at the time. Now, watching it as a parent, I realize how early girls learn to use charm and emotional labor to navigate systems that weren’t built for them. It’s a reminder that being clever is powerful—but I want my daughter to know she doesn't have to manipulate her way into fairness. She deserves it, just as she is.

Watching it now, I see everything I missed the first time. The commentary on class. The emotional labor Cher carried. The way Dionne protected her boundaries and her people. The moments of vulnerability disguised as confidence. And the quiet resilience of girls learning to take up space.

Back then, I watched Clueless for the quotes and the clothes. Now, I watch it and see my younger self, my current self, and my daughter—all tangled together in the journey of becoming.

We’re still figuring it out. And maybe that’s the point.