Behind the Meaning of Kelsea Ballerini’s “How Do I Do This?”

Kelsea Ballerini’s Rolling Up the Welcome Mat sees her explore the downfall of a marriage, find a way to pick herself back up again, and trek on to new beginnings.

Each of the tracks acts as one chapter of Ballerini’s life over the last couple of years. Songs like “Just Married,” “Blindsided,” and “Leave Me Again” cover the heartbreak and healing sections of Ballerini’s story. One track on the “(For Good)” deluxe version of the EP, “How Do I Do This?, sees Ballerini expound on her newfound identity and introduce a new character into the mix. Check out the meaning behind this track, below.

[RELATED: Kelsea Ballerini Is Taking Her Time on Her Next Album, Wants to Get it “Right”]

Behind the Meaning

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
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

Ballerini isn’t afraid to share her personal life with her audience. Much like an inspiration of hers, Taylor Swift, Ballerini prefers to shed some light on the things in her life that will undoubtedly make headlines–like a new relationship.

In 2023, news broke that Ballerini started dating Outer Banks actor Chase Stokes. This was her first major, public relationship following her divorce from fellow country singer Morgan Evans. Naturally, her fans were intrigued.

Instead of letting the online discourse run rampant, Ballerini decided to detail the beginning of their relationship in “How Do I Do This?”

I’m scared of looking stupid
Said I, I’m rеady 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’

In this track, Ballerini aligns herself with any person about to go on a nerve-racking first date–particularly in the aftermath of a major heartbreak. She sings about feeling nervous to put herself out there again and find love for a second time around. Despite her trepidation, she concedes to push forward. I think it’s probably time to keep it movin’, she sings.

While famous musicians will always be somewhat untouchable figures, Ballerini manages to ground herself with this song. Almost anyone could listen to this song and find an element of themselves in it–the mark of a powerful songwriter.

Revisit this track, below.

Photo by Manny Carabel/Getty Images for Audacy’s Leading Ladies 2024