Woman Wears Sweatpants to ‘Super Casual’ Family Brunch, but Her Boyfriend Had Other Plans

One Saturday morning in December, Kari Scott got out of bed and dressed for what she expected to be a low-key family brunch at her grandmother’s house with her now-fiancé, David Kaplan.

The 28-year-old kept it comfortable, slipping into pink sweatpants and one of Kaplan’s sweatshirts without a second thought.

When she came downstairs, she noticed Kaplan looked a little more put together than usual—but she didn’t read into it. She hopped in the car, still assuming the day would be simple and relaxed.

What Scott didn’t realize was that the brunch was only the beginning. The plan for the rest of the day had been swapped for something much bigger—and her loved ones were already in place, ready to capture it.

On the drive back, Kaplan’s sister called sounding frantic, claiming she’d lost her keys along the Lake Shore Path in Chicago and needed help. Scott wasn’t thrilled about the detour, but they went anyway.

As they walked toward the area where the keys were supposedly dropped, Scott spotted rose petals arranged into a heart—and a photographer nearby. In an instant, everything clicked.

Her first reaction wasn’t a romantic movie moment. It was panic about what she was wearing.

Oh my god. I look horrible. Oh my god. I’m in my sweatpants, she remembers thinking.

Still, she leaned into the moment—because the person in front of her mattered more than the outfit on her legs.

Kaplan dropped to one knee. Scott said yes.

Almost immediately, both families stepped out from behind a small nearby building, cheering as the surprise turned into a full-on celebration. Champagne popped. Hugs went around. What started as “just brunch” quickly became an engagement party.

Later, Kaplan admitted he had even warned his sister that Scott was wearing sweatpants—assuming she’d at least be in leggings or a sweater. But by the time the message came through, it was too late to pivot.

And once he proposed, Scott says the outfit didn’t matter anymore.

She was stunned to see so many people she loved gathered in one place—but in the best way possible.

Because Scott’s sister came prepared, she brought a backup outfit: white slacks and a white sweater. That way, the couple could retake proposal photos if Scott wanted something more “photo-ready.”

But Scott wasn’t embarrassed—she thought the whole thing was perfectly fitting.

After all, she joked, they’re likely going to spend a big chunk of their lives together at home in sweatpants anyway—so why not make that part of the story, too?

Even after changing for a second round of photos, she chose to share the original proposal shots online, embracing the humor and the authenticity of the moment.

And for her, that’s the point: she’s relaxed on Saturday mornings, and dressing up just to fit an expectation wouldn’t feel like her—especially on a day that was about being loved exactly as she is, pink sweatpants included.