The Meaning Behind “Sally, When The Wine Runs Out” by Role Model and Laughing at the Awkwardness of Dating Again

Role Model, born Tucker Pillsbury, released “Sally, When The Wine Runs Out” on the deluxe edition of his second studio album, Kansas Anymore. The album’s title nods to The Wizard Of Oz and a sense of being lost in a strange place. And in “Sally”, Pillsbury dips his toes back into the dating pool, and things get awkward for the singer.

And if you’ve been away from dating for a while, the reality can seem like you’ve woken inside the Land of Oz. Co-written with Noah Conrad, Annika Bennett, and Harrison Whitford, “Sally” follows Pillsbury falling for a girl knowing she’s probably only into him when they’re drunk. Then he pleads with her: please don’t change your mind.

Sally’s Born Again and Raging

In the opening verse, Pillsbury meets a girl at a dive bar. But he’s not prepared for the girl’s epic drinking. Though she’s found Jesus, she likes to party. Still, he’s got to keep up.

I met Sally at a late-night dive bar.
She don’t dance, but she downs her drinks,
Heard through a friend she’s a born-again wildcard.
She was telling me wild things.

So he goes home with the girl. But he becomes anxious and then drops some emotional baggage while they are stopped at a red light.

Lives down the street past the 7-Eleven.
Just close enough that I spent the night,
She grabbed my hand at the intersection.
I spilled my guts at the red light.

He’s smitten but worried she’ll change her mind when the buzz wears off.

Sally,
That feeling’s coming around.
Please don’t go falling in love,
Then disappear when the wine runs out.

“Hesitant and Doubtful”

“Lyrically, it was me being hesitant and doubtful,” Pillsbury told Billboard.

But the dusty tune also feels light and upbeat. And any anxiety Pillsbury may have felt has been replaced by the feel-good vibe of laughing off how much the awkward and the absurd often accompany dating. Especially for someone who’s out of practice.

Aw, sh*t, here we go again, I’m falling headfirst,
Ankles hit the two-step, Sally makes my head hurt.

Photo by Erika Goldring/Getty Images