Jelly Roll Wife, Girlfriend & Affair History: Who Has He Dated?
Jelly Roll and his wife Bunnie XO are getting divorced. That has placed scrutiny on Jelly Roll and his girlfriend, affair and dating history.
Who has Jelly Roll dated? Unlike a lot of singers, he doesn't have a lengthy history of high-profile girlfriends. His dating history, though, includes a long-term marriage to social media influencer Bunnie XO, kids with two other former girlfriends, and a previous affair. TMZ reported that Jelly Roll "filed for divorce from his wife in May in Tennessee."
He married wife Bunnie XO in 2016 and touted their marriage on Instagram. "Somebody asked me what's the secret to our marriage the other day. I didn't even have to think about - it's simple - we are comfortable having uncomfortable conversations," Jelly Roll wrote on Instagram in 2020. "We have learn to laugh at the small sh*t, and above everything, we don't take anything too seriously. This woman is my backbone in life, she's beautiful, smart, witty, and you wouldn't believe how silly she really is.
Jelly Roll Had an Affair 3 Year Into His Marriage to Bunnie XO
Jelly Roll's dating history unfortunately includes a previous girlfriend on the side.
"He had an affair three years into their marriage," an issue that he and his wife discussed publicly, according to Hello!
"When I found out about it, it was just so heartbreaking," Bunnie XO said of his affair to Kelly Clarkson, according to Hello!, although she did not name the woman. "Instead of looking at him and being like, this is your fault, you know. I looked within myself, and was like, why do I keep attracting these types of men?"
Jelly Roll also spoke about the affair on a podcast called Human School.
"One of the worst moments of my adulthood was when I had an affair on my wife," he said. "Because it was the first time that I was like, 'I really can't get this right at all. I know I'm in love with this woman.' It just really, really, really blew me back."
At the same time, although she said they didn't have an open marriage exactly, Bunnie XO revealed in her book that she and Jelly Roll did not practice monogamy at all stages of their marriage. In fact, she revealed that she continued working as an escort while touring with him, according to Billboard.
"J was used to having multiple relationships at the same time with different women. So when we first got together, we both frowned upon monogamy," she wrote in her book, according to Billboard. "That's not to say that we agreed to go (expletive) whoever we wanted whenever we wanted - to me that's what an open relationship is, and we aren't in one. But if a girl wanted to come home with us, we more than likely wouldn't turn her down. Now, here comes the part that might surprise you. J has always told me that I can sleep with other men if I want to…. We both live by the motto that we aren't each other's possessions and consider our relationship to be free, not open. Free will. Which means: I'll give you the world sexually, but don't (expletive) lie to me or ever let me be the last to know something."
According to Billboard, Jelly Roll's affair, which lasted 10 months, upset Bunnie XO in part because he lied about it.
Jelly Roll Has 2 Kids, Bailee Ann & Noah, With Previous Girlfriends
According to NBC News, Jelly Roll's daughter, Bailee Ann, is "from a previous relationship" and was born in 2008. He also has a son named Noah, born in August 2016, "to a woman with whom the singer had previously been involved."
He obtained custody of Bailee Ann in 2017, according to NBC News.
What about Noah? One week before he married Bunnie XO, Jelly Roll "welcomed a son with another woman," TMZ reported.
Jelly Roll's Son Noah's Mom Is Named Melisa Ann Cowell
According to TODAY, Jelly Roll's son Noah was born in 2016 to a woman named Melisa Ann Cowell.
"Welcome to earth," Jelly Roll wrote of the boy on Facebook, sharing a photo of the newborn baby. Noah has appeared in TikTok videos with Bunnie XO.
Who Is Bailee Ann's Mom? Jelly Roll's Former Girlfriend Is Named Felicia Beckwith
According to American Songwriter, Bailee Ann's mom is named Felicia Beckwith.
In 2020, "Bailee's biological mother, Felicia Beckwith had just gotten out of jail and seemed to be in recovery," American Songwriter wrote, when Bailee said on Bunnie XO's podcast that her mom "popped up two days before my 12th birthday. I guess we just kinda started building a relationship from there."
Bailee said she spent the summer with her mom but alleged that Beckwith "was drinking and smoking pot with her young daughter," American Songwriter claimed, quoting Bailee as saying, "OK, this is whatever, you're just a cool mom, you're letting me drink, you're letting me smoke weed. This is cool." She then alleged that her mom tried introducing her to hard drugs.
"I was never sober for a good 8-month period," Bailee said, but then she decided to get sober. The 2024 podcast episode in which Bailee made these allegations is called "strength and healing."
According to Fox News, Jelly Roll said in 2025 on another podcast that Beckwith "was reportedly arrested on felony drug charges." The outcome of the case or where it occurred is not clear. Jelly Roll was incarcerated when Beckwith gave birth to Bailee. She is described by NBC News as his ex.
Who is Jelly Roll's wife, Bunnie XO?
Bunnie XO has 8.2 million followers on TikTok, where she calls herself a "Fairy Godmother" and "Trailerpark Barbara Walters." She runs a podcast called Dumb Blonde Pod. On YouTube, her podcast has more than 1 million subscribers. Her real name is Alyssa DeFord. On Instagram, she has 2.5 million followers.
According to her IMDb profile, her show "digs deep into the past of her guests, gives light to current issues, and even has her guests play outlandish games." She met Jelly Roll "in 2015 while she was attending one of his concerts in Las Vegas at the Country Saloon," NBC News reported.
"I'm not going to act like I shot my shot. [Bunnie XO] kind of shot hers," Jelly Roll told The Golden Hour podcast. The married in Las Vegas in 2016 right after he proposed. "We got married kind of randomly," he said on the podcast.
This story was originally published by Men's Journal on Jun 16, 2026, where it first appeared in the Entertainment section. Add Men's Journal as a Preferred Source by clicking here.
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This story was originally published June 16, 2026 at 10:26 AM.