Second chances are possible, and Jelly Roll is living proof of this.

Before he was dominating charts across all genres, the Antioch, Tennessee native, 40, grappled with substance use issues and incarceration. Since shooting to international fame in 2023, Jelly has made a point of extending a hand to those in all-too-familiar circumstances. In the latest example of this, the “I Am Not Okay” crooner has gone viral for the generous gift he bestowed upon a Canadian fan.

She Thought She Was Just Going To Meet Jelly Roll

Six years ago, Michelle Boissonneault was battling addiction and homelessness in downtown London, Ontario. On April 25, she will celebrate three years of sobriety. These days, Boissonneault has transitioned out of homelessness and works with a local community outreach group to help others experiencing similar situations.

While out volunteering Sunday (March 23,) Boissonneault was shocked to learn that a man she had just gifted new shoes was in fact Zachery Dereniowski, known online as YouTuber MDMotivator. Dereniowski aims to spread kindness and raise mental health awareness by handing out money and gifts to “lost people.” This time, he surprised the Jelly Roll fan with VIP concert tickets.

That very night, Boissonneault found herself embracing the “Need a Favor” singer backstage at the Canada Life Place in London, Ontario. Already firmly on cloud nine, she had no idea of an even bigger surprise in store.

“Yours is the type of story that we write songs for,” Jelly told her before handing over the keys to a brand-new vehicle.

“My Heart Could Burst”

Two days later, Boissoneault let a well of gratitude flow out of her in a poignant social media post.

“Sunday March 23rd Is a day that I will honestly never ever forgot,” she wrote. “Still hard for me to put into words the amount of gratitude and love I feel right now.”

Of Jelly Roll, the Ontario woman wrote, “You are such a light, an incredible down to earth, caring man! Thank you for the tears we shared, the laughs, and the words of wisdom and praise, meeting you was like ya know, having a chat with an old friend!!! THANK YOU.”

Summing up the post, she said, “My heart could burst it’s so full.”

Featured image by Tibrina Hobson/Getty Images