Honestly, if you're expecting a private jet to Paris or a rented-out baseball stadium, you’ve come to the wrong place. When Matthew Koma finally decided to pop the question to Hilary Duff in May 2019, he didn't go for the over-the-top Hollywood spectacle. He went for sweatpants.
Most celebrity engagements feel like they were staged for a camera crew, but the Hilary Duff proposal was different. It was messy, tired, and relatable in a way that’s actually kind of annoying if you’re still waiting for your own "storybook" moment.
The "I’m Too Tired for This" Walk
Here is the scene: It’s a random Tuesday in Brooklyn. Hilary has been on set for Younger since 4:00 AM. She gets home, her brain is fried, and all she wants to do is eat dinner in bed and binge-watch Game of Thrones.
Enter Matthew Koma.
He’s acting weirdly insistent about going for a walk. Hilary, being a human person who has worked a 14-hour day, basically says "no way." She eventually negotiates: she will go on this walk, but only if she can wear her sweatpants. Matthew, probably sweating bullets at this point, agrees immediately.
They head out to a park near their apartment in Williamsburg. It’s right on the water, gorgeous, and surprisingly quiet for New York.
The Book of "Us"
While they’re walking, Matthew pulls out this book. It’s not just a notebook; he’d been working on it for months. He’d commissioned an artist named Shane to illustrate their entire relationship—the ups, the downs, and the "on-again, off-again" periods that actually defined their early years.
He told her they needed to keep record of their story so they wouldn't forget anything as they got older. It was a gift for their kids as much as it was for them.
The most personal detail? The "half-orange."
There is this Spanish expression, media naranja, which refers to your soulmate—the other half of your orange. It’s an inside joke they share. On the very last page of the book, there was a little sketch of an orange. Hilary had to lift a small paper flap on the drawing, and tucked inside a hidden compartment was the ring.
The Ring: A Lesson in "Quiet Luxury"
While her first engagement ring from Mike Comrie was a massive 14-carat radiant-cut diamond that basically needed its own zip code, the ring Matthew chose was far more "Hilary 2.0."
It’s a cushion-cut diamond, estimated to be around 3 to 4 carats.
- The Cut: Cushion-cut (square with rounded edges).
- The Band: A delicate split-shank solitaire.
- The Vibe: Modern, minimalist, and way more practical for someone chasing toddlers around.
It’s an E or F color grade—basically colorless—and sits on a thin white gold or platinum band. It’s the kind of ring that looks like it belongs on a woman who has found her rhythm, rather than a starlet trying to make a statement.
Why Everyone Still Talks About It
We’re used to seeing influencers stage their engagements with professional lighting and 4K drones. The Hilary Duff proposal worked because it was the opposite of a "brand activation."
Matthew admitted later that once he got down on one knee, he completely forgot every single word of the speech he had prepared. He basically just told her she was his best friend.
It’s also worth noting the timing. They had already welcomed their daughter, Banks, seven months prior. They had been through the "breakup and makeup" cycle three different times before it finally stuck. There’s a certain maturity in that—knowing that the person you want to watch Game of Thrones with in your sweatpants is the same person you want to build a life with.
👉 See also: John Legend Wife: Why Chrissy Teigen Is Still the Most Relatable (and Polarizing) Person on Your Feed
Breaking Down the Timeline
- 2015: They meet while working on her album Breathe In. Breathe Out.
- 2017: Red carpet debut, followed by a brief breakup.
- 2018: They reunite for the third time and welcome daughter Banks.
- May 2019: The proposal in Brooklyn.
- December 2019: An intimate "winter solstice" backyard wedding.
Lessons from the Duff-Koma Playbook
If you’re planning a proposal or just obsessed with celebrity weddings, there’s a lot to learn from how they handled this.
First, stop trying to make it "perfect." The fact that Hilary was exhausted and cranky actually made the moment more memorable. Real life isn't a curated Instagram feed, and your proposal shouldn't feel like one either.
Second, the "story" matters more than the "stone." The book Matthew made cost significantly less than the diamond, but it’s the thing she cried about in her Vogue interview. Personal history is the ultimate luxury.
Check your local independent bookstores or artists on platforms like Etsy if you want to commission a custom "relationship book." It turns a "random Tuesday" into a family heirloom.
If you're looking for ring inspiration, look for "cushion-cut solitaire with a split shank." It’s a timeless style that won't look dated when you're looking at your photos twenty years from now. Focus on the quality of the stone over the size of the rock. Minimalist settings allow the diamond to catch light from all angles, making a 3-carat stone look way more impressive than a cluttered 5-carat design.