Kelsea Ballerini Shares Black Dress She Wore on 1st Chase Stokes Dates

Kelsea Ballerini is taking it back to the beginning of her romance with now-boyfriend Chase Stokes.

“Happy weekend, here’s a video I sent to my best friend before my first date with Chase,” Ballerini, 29, captioned a Saturday, August 19, TikTok video as she hyped herself up in the mirror.

In the clip, Ballerini posed for a mirror selfie to show off her “look.” The country singer rocked a black, floral minidress and coordinating booties “because we’re trying to be [a] cool girl.”

“He’s picking me up and we’re going to a sushi place and I’ll call you tomorrow for a full update,” she added.

Kelsea Ballerini and Chase Stokes’ Relationship Timeline

Ballerini documented said date in her new song “How Do I Do This,” which dropped earlier this month. Her lyrics even specifically mention the “little black dress” she wore and doing “last looks in the mirror” before her beau arrived.

“I’m scared of looking stupid / Said I’m ready now, I gotta prove it / Got a little black dress, I wanna use it,” Ballerini sang. “And maybe lose it on the floor that ain’t mine / I think it’s probably time to keep it movin’.”

Ballerini dropped “How Do I Do This” on the extended edition of her Rolling Up the Welcome Mat EP, which is titled, Rolling Up the Welcome Mat (For Good).

“It’s about the nerves of going into a very unknown world,” Ballerini exclusively told Us Weekly earlier in August of the post-breakup song. “And, to me, I felt like since I hadn’t really gotten to share my story in my perspective on what had happened in my life yet, that needed to come second. That is part two. I felt like I really wanted to talk about, you know, the breakup, and let that kind of live in one piece. And then if I ever decided to do what we’re doing now — Rolling Up the Welcome Mat (For Good) — then that would be kind of the extension of the story.”

Kelsea Ballerini’s ‘Interlude’ & ‘How Do I Do This’ Lyrics Explained

Stokes, 30, also praised Rolling Up the Welcome Mat (For Good) upon its release, sharing a throwback snap of Ballerini in the dark gown. “Little black dress: used 🥺,” she wrote via Instagram Story at the time, resharing his note.

Ballerini filed for divorce from Morgan Evans in August 2022 after four years of marriage, and the split was finalized the following November. Less than one month later, she connected with the Outer Banks star.

“I slid into his DMs,” Ballerini said during a February appearance on the “Call Her Daddy” podcast. “He shoots [Outer Banks] in Charleston, and my manager lives there. He was like, ‘You know who’s really cute, like, when you’re ready? Chase.’ I was like, ‘You’re so right.’”

Everything Kelsea Ballerini and Morgan Evans Have Said About Their Divorce

She continued at the time: “His handle is ‘hichasestokes’ and I just said, ‘Hi Chase Stokes.’ We’re manifesting, baby!”

The lyrics of “How Do I Do This” also mentioned Ballerini’s manager, who was responsible for the fixup. “They say to get out with the old you get in with the new / And I haven’t been on a date since I was 22,” she sang in the first verse. “My friend has a friend, and they say they’re my type / And then they’re texting me once, and then they’re texting me twice / Sayin’, ‘Are you free Saturday? I know a spot.’”

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The track ended with Ballerini “freaking out” because it was “7 on the dot” — exactly when her date was scheduled to arrive.

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