WATCH: Jessie James Decker Joins Jo Dee Messina For ‘Lesson in Leavin’’ Duet

This impromptu “stair session” was a full-circle moment for Decker.

By

Madeleine O’Connell

| Posted on

December 17, 2025

at

12:12 pm

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Jessie James Decker, Jo Dee Messina

Jessie James Decker recently hosted country music icon Jo Dee Messina at her home for her intimate “stair sessions” series, where the pair of artists traded acoustic harmonies on Messina’s hit “Lesson in Leavin’.”

The stripped-down moment gave fans a glimpse of the magic behind the beloved ‘90s country tune as both of the female singers effortlessly traded lines and let their vocals echo throughout the home. Together, they brought the classic country breakup story to life by leaning into the themes of empowerment and moving on from the pain of someone’s repeated mistakes.

Jessie James Decker, Jo Dee Messina
Jessie James Decker, Jo Dee Messina

“Somebody’s gonna give you a lesson in leavin’/ Somebody’s gonna give you back what you’ve been givin’/ And I hope that I’m around/ To watch ’em knock you down/ It’s like you to love ’em and leave ’em/ Just like you loved me and left me/ It’s like you to do that sort of thing/ Over and over again/ You’re a fool-hearted man,” they sang on the opening lyrics.

Originally called “A Lesson in Leavin’,” the tune was written by Randy Goodrum and Brent Maher, and first recorded by Dottie West in 1979 for her Special Delivery album. Messina later retitled the song to “Lesson in Leavin’” and released it as a single in 1999 from her second album, I’m Alright. The track became a major hit, spending seven weeks at No. 2 on the Billboard Hot Country Singles & Tracks chart.

Reflecting on the experience, Decker called it a “pinch-me moment.” She reminisced about being a longtime fan of Messina’s as she recalled driving to school as a child with the windows down, belting out her catalog of iconic tunes.

She wrote, “Brought me back to my childhood driving to school with the windows down in the truck singing her songs at the top of my lungs just thinking about how cool she must be (and she is, as cool and amazing as it gets)”

The “I Still Love You” singer added that she “never imagined” that she would get the chance to not only sing but also to simply spend the day hanging out with such a beloved and well-known member of the country music community.

“Love you Jo Dee!!!,” she concluded.

Messina matched her excitement and commented a kind message in response. “This was SOOOOOO fun !!! Thank you JJD for such a great day ❤️❤️”

The pair made use of their day together and filmed several videos for social media. Another teaser clip Decker posted found her standing at her door, and mouthing along to the trending audio that says, “Cause it’s iconic and I love to do iconic sh**,” in response to the question, “Why is there a country music icon at your house?” The sound then switches to include a snippet from another one of Messina’s iconic tracks, “Heads Carolina, Tails California” as she makes her way into Decker’s home with excitement written all over her face.

For Jessie James Decker, this day turned out to be a full-circle moment as she got to connect with one of her childhood idols, while Messina got to see the impact of her music on the next generation of country stars.

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Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.