“Love has no age. But does it still have boundaries?”
In a world already full of surprise reunions, late-in-life memoirs, and sudden goodbyes, few stories have stirred the country music world quite like this one: the rumor that Jessi Colter — the soulful outlaw queen and widow of Waylon Jennings — is preparing to say “I do” once again… at the age of 81.
The alleged groom?
A name few outside Arizona might recognize, but one that echoes quietly in Jessi’s past: Thomas Avery, her childhood bandmate from back when they both played gospel music in tiny churches under the blazing desert sun.
“They sang together before they knew what love really meant,” an unnamed source told Country Echo. “Now, they’re singing again — maybe for the last chapter.”
A Love Reignited in the Shadows
Reports first began swirling when the two were spotted walking hand-in-hand outside a retirement music studio in Sedona, Arizona, where Jessi has been quietly recording what many believed would be her final album. Witnesses say the chemistry was unmistakable.
“They weren’t just old friends catching up,” said another local. “They looked… in love. Real, uncomplicated love.”
According to insiders close to the Colter family, Thomas — now 83, a retired music teacher who never remarried after his wife passed away in 2009 — reconnected with Jessi during a small gospel benefit concert she organized in April. One duet turned into several late-night rehearsals, and the rest, as they say, might be history.
Shooter Jennings Responds: “This Doesn’t Feel Right”
Not everyone is celebrating. Shooter Jennings, Jessi’s only child and himself a respected musician, reportedly found out about the rumored engagement through a tabloid tip-off rather than a family conversation.
“He’s not angry,” a close friend said. “He’s just… confused. Hurt. It’s not about the man — it’s about the moment. He’s always protected his mother’s legacy, and this came out of nowhere.”
Shooter has yet to issue a public statement, but on July 12, he posted a cryptic tweet that has since been deleted:
“Some chapters shouldn’t be rewritten. Especially not with someone else’s pen.”
Fans were quick to speculate about the meaning, and the comment section quickly turned into a battlefield of opinions.
The Internet Reacts: “Let Her Love Again” vs. “This Is Disrespectful”
Social media exploded with mixed reactions, splitting fans into two distinct camps:
Team Jessi praised the idea of second chances, flooding her fan pages with comments like:
“If anyone deserves happiness, it’s her. Let her live.”
“Love doesn’t die with age. Sometimes it just waits.”
Team Waylon, however, voiced concern that this move tarnishes the sacred memory of the outlaw love story between Jessi and Waylon Jennings — a relationship that survived addiction, fame, chaos, and ultimately, death.
“She was his anchor. This feels like betrayal.”
“Waylon gave her his last breath. What would he think?”
One fan wrote on Reddit:
“I’m torn. I love her. I want her happy. But this feels like erasing something timeless.”
But Is It Even True?


Here’s where the mystery deepens: No official wedding has been confirmed. No ring has been shown. No formal announcement has come from Jessi’s representatives.
So where did the story come from?
“I think people want to believe in love stories,” said Mary T., an editor at Southern Dust, a magazine that first ran the rumor. “And when you’re 81, people either expect you to fade quietly — or shock them. Jessi’s never been the quiet type.”
In fact, one friend close to the family hinted that the rumor might have been exaggerated from a private “commitment ceremony” — something deeply personal and symbolic, not legally binding. Something just between two hearts with nothing left to prove.
What Jessi Herself Might Say
Though she’s yet to speak publicly on the issue, those who know Jessi best say she isn’t surprised by the uproar.
“She’s always walked her own road,” said Bonnie Owens, a longtime family friend. “She loved Waylon fiercely — but that doesn’t mean her story ended with him. She’s still living. Still singing. And maybe… still loving.”
Jessi Colter, the woman who once stood quietly in the chaos of the Outlaw movement, is now standing in a very different kind of storm. One not of addiction or fame — but of public judgment and private longing.
The Final Question: Can You Love Twice in One Lifetime?
If the rumor proves true, then Jessi Colter is not rewriting her story — she’s finishing it, in her own words.
“Maybe this isn’t about replacing Waylon,” one fan wrote. “Maybe it’s about Jessi finally choosing something just for her.”
And maybe, just maybe, there’s room for more than one great love in a lifetime. Even if the world isn’t ready to watch it happen.
Until then, the desert winds in Arizona carry whispers — of old songs, of new vows, and of a woman who may just be brave enough to believe that love, like music, never truly ends.