Why Kelsea Ballerini's Final RUTWM Chapter Is A Full-Circle Moment

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Kelsea Ballerini is getting ready to share “the final chapter” of her Rolling Up The Welcome Mat (For Good) era. The award-winning singer-songwriter revealed on Thursday afternoon (November 30) that the music video for “How Do I Do This,” an added track on her extended EP about beginning to date again after divorce, will premiere Friday evening (December 1).

Fittingly, the “How Do I Do This” music video will make its debut at 7 p.m. (“on the dot”), referencing the song’s lyrics. Some eagle-eyed fans also couldn't help noting that the premiere date happens to land on the one-year anniversary of Ballerini sliding into boyfriend Chase Stokes’ DMs on Instagram. The “HEARTFIRST” star has previously shared that she and Stokes began talking after she wrote “hiii chase stokes” in a message on Instagram, apparently at 1:07 a.m. on December 1, a previously-shared screenshot shows.

“i’m freaking out like OH MY GOD cuz now the how do i do this music video comes out tomorrow at 7 (pm) on the dot !!!! get your little black dresses ready,” Ballerini wrote in her caption on Instagram as she shared the trailer for the soon-to-premiere music video. “The Final Chapter” appears on screen as the trailer plays, and Ballerini appears to get ready for a date.

“I'm scared of looking stupid/ Said I, I'm ready now, I gotta prove it/ Got a little black dress, I wanna use it/ And maybe lose it on the floor that ain't mine/ I think it's probably time to keep it movin’/ I talk a big game, that I'm scared of losin’/ Everything I knew about love is ruined, it's so confusing/ So, how do, how do I do this?
“I'm calling Kelly for a talk/ Like is it wrong to take a shot?/ I’m freaking out, like, oh my God/ ‘Cause now it's 7 on the dot”

Ballerini released the original Rolling Up The Welcome Mat and an accompanying 20-minute short film in February. The deeply personal project shares her story of heartache and healing amid her divorce last year, after nearly five years of marriage. Ballerini released the extended version of the EP, Rolling Up The Welcome Mat (For Good), in August, making a few updates to some previously-related tracks and adding “How Do I Do This” to the collection.

Ballerini, who confirmed her relationship with the Outer Banks actor shortly after releasing the original RUTWM, has also hinted at the next chapter in her music. Earlier this week, she brought surprise guests Karen Fairchild and Hillary Lindsey to the legendary Grand Ole Opry stage in Nashville, Tennessee, performing a heartfelt ballad the trio wrote together called “To The Men That Love Women After Heartbreak.”

“The reality is, I’ve been singing about a chapter of my life that is far past me now,” Ballerini said, in part, on the Opry stage before performing the song. “And I’m writing about the chapter of life that I’m in, and it looks very different, and I kind of wanted to share a bit of it now. I’m very gently and slowly starting to make the next record. I really want to take the time to handle it with care.”