Why Gilmore Girls Still Teaches Me About Real Freedom (and Real Love)

Revisiting Gilmore Girls this fall, I’m learning that true freedom isn’t about doing whatever we want — it’s about choosing the good.

(Photo: Wikimedia Commons / Fair use)

Every fall, without fail, I cue up Gilmore Girls. It’s just the ultimate cozy fall show. The leaves in Stars Hollow, the endless coffee, sweaters, scarves and iconic Friday night dinners — it all screams autumn in a way no other series really does. Recently, while celebrating 25 years of Gilmore Girls at the Emmys, even Lauren Graham joked, “25 years ago, a show called Gilmore Girls premiered and apparently took the season of fall hostage.” 

But the older I get, the more I watch it with different eyes. As a teen, Lorelai seemed like the coolest mom alive. She’s quick-witted, rebellious, the perfect best-friend-mom. Now? Whew. I look at her and think, “I’m so glad my mom is nothing like you.” She hides truths, avoids responsibility and often pushes Rory into situations without much foresight. Meanwhile, the classy Emily Gilmore, forever painted as the controlling villain, actually comes across as someone trying (albeit stiffly) to provide Rory with some stability and structure during incredibly formative years. 

And here’s the kicker: Lorelai’s questionable choices end up paving the way for Rory to make her own questionable choices. (Rory, why did you drop out of Yale??) It’s like generational déjà vu. 

Now that I’m an expectant first-time mom, I can assure you I would never make those mistakes. Lorelei makes so many questionable choices in front of her daughter and constantly avoids structure for the sake of being “fun.” And no, my kid is not dropping out of Yale. (Hold me to that one in 20 years.) 

So, where am I going with all of this? 

Often, we think of freedom as doing whatever we want: no rules, no boundaries, total independence. But that’s not real freedom. True freedom is the power to choose the good, to align our will with God’s will. That’s where purpose and joy are found: in choosing love, truth and ultimately, union with him. God desires us to live in that kind of freedom, but he never forces himself on us. He invites us into relationship with him, he pursues our hearts and then he leaves the choice to us. 

Which brings me back to Lorelai and Emily. Lorelai represents love and freedom, but often without boundaries, which leads Rory to make poor choices. Emily represents discipline and structure, but often without tenderness. In reality, God the Father gives us love with both mercy and justice. Which may be the hidden beauty of Gilmore Girls: Rory bouncing between those poles, learning (sometimes the hard way) that real freedom isn’t about casting off all limits but about learning how to live well within them. 

And that’s why, every fall, I come back to Stars Hollow — not just for the vibes, but for these messy, complicated lessons that land differently as the years go by. And now, with a baby on the way, I find myself hoping I can offer both: Lorelai’s warmth and Emily’s structure. Mercy and discipline. Freedom and truth.