Kelsea Ballerini’s ‘How Do I Do This’ Video Teases Chase Stokes 1st Date

Kelsea Ballerini slipped into her best little black dress as she prepared for her first date in her official “How Do I Do This (The Final Chapter)” music video.

“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,” Ballerini, 30, starts off singing in the Friday, December 1, video, while wearing sweatpants following her divorce from Morgan Evans. “My friend has a friend and they say they’re my type / And then they texted me once / And then they texted me twice / Saying, ‘Are you free Saturday? I know a spot’ / So, I typed out a couple million ways to respond / But I landed with ‘Yes’ / S—t, so where the hell is my dress?”

After nervously texting her future date — which she’s previously hinted was now-boyfriend, Chase Stokes — Ballerini gets dolled up in a Cinderella blue dress while dreaming about the possible new romance. She continues to primp and sing to herself in the mirror before chopping off her long locks as part of her new phase post-divorce.

In the video, the country singer rocks multiple fairy tale gowns in her room before settling on a sexy LBD and sipping wine in the bathroom. When the doorbell rings and Ballerini smirks in her mirror and then pauses before walking to meet her new man.

Ballerini released the song “How Do I Do This (The Final Chapter)” in August as part of her Rolling Up the Welcome Mat (For Good) EP.

The initial album came out in February and documented Ballerini’s divorce from Evans, 38, which was finalized in November 2022. The twosome were married for nearly five years before their split.

While many of the tracks on the record recalled the hard times Ballerini had to overcome after heartbreak, “How Do I Do This,” is a song about her moving on with boyfriend Stokes, 31, and the nerves she felt before going out on that first date.

“It’s about the nerves of going into a very unknown world,” Ballerini exclusively told Us Weekly in August of the 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.”

The Grammy nominee explained: “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. And especially now, I’ve been in a new relationship for a while now, and people have seen that. So I feel like it’s a really appropriate time to catch everyone up and to be able to move the narrative from the past to the present.”

Ballerini touches on the butterflies she felt stepping into her post-divorce dating era in the track, singing, “Like, is it wrong to take a shot? / I’m freaking out like ‘Oh, my God’ / ‘Cause now it’s 7:00 on the dot.” She also name-drops Kelly Clarkson in one verse, revealing she called Clarkson, 41, “for a talk” before the big night.

Ballerini and Stokes were first linked in January while attending the College Football Playoff National Championship in Los Angeles. Ballerini confirmed the relationship one month later during an appearance on the “Call Her Daddy” podcast, sharing that she slid into the Outer Banks star’s DMs.

The pair made their red carpet debut in April at the CMT Music Awards in Nashville and have been giving fans glimpses at their romance ever since.

“We are both very much so golden-retriever energy most of the time, but we both have a little bite in us, and we’re both incredibly driven,” Ballerini told Nylon of Stokes in October. “He is the first person I’ve been in a relationship with that I feel like is not my complete opposite.”