Jelly Roll Reveals His Surprising Connection to Taylor Swift — and Why He Was ‘So Bad’ When He Met Her (Exclusive)

The country star talks to PEOPLE in this week’s issue about being starstruck by Swift

He may be a Grammy-nominated country star, but even Jelly Roll gets starstruck sometimes.

The “Winning Streak” singer, 39, opens up to PEOPLE in this week’s issue about his Taylor Swift meet-cute at the 2024 Grammy Awards, and how he was nearly rendered speechless by his run-in with the pop star.

Jelly says that upon seeing Swift, 34, he gathered up his courage to tell her about how he used to push his daughter Bailee, now 16, on the swings at a children’s playground that she helped fund in Hendersonville, Tenn.

“I take a ridiculous, probably abnormal, amount of pride in being from Nashville, so anytime I can link a Tennessee connect, it tickles me,” he explains. “Taylor lived in Hendersonville for a while, and she had bought a playground. I used to push Bailee on that swingset that Taylor donated to Hendersonville. I wanted to tell her that when I met her, but I was so nervous I couldn’t even remember what swingset it was.”

Bailee Ann and Jelly Roll at the Nickelodeon's Kids' Choice Awards 2024 held at Barker Hangar on July 13, 2024 in Santa Monica,

In 2010, Swift — who went to high school in Hendersonville — teamed up with Little Tikes Commercial to rebuild the Kids Kingdom playground at Memorial Park, which had been destroyed by flooding. A press release at the time said the “Fortnight” singer donated $100,000 to the project to help bring it to completion. The playground now includes castle-inspired slides with flags bearing Swift’s signature.

Jelly says that even though Swift was the one to approach him at the Grammys, he was still left tongue-tied.

“My wife [Bunnie Xo] said, ‘I think Taylor’s coming over to holler at you.’ It was like the Red Sea parted for her,” he recalls. “I’m looking at Taylor Swift and I have a reason to explain to her why I like her so much, and I’m going, ‘You built the swingset somewhere, my daughter, I pushed her on it.’ I did so bad! Definitely was at a loss for words in that moment.”

jelly roll cover

Their meeting was captured on video by Bunnie, who shared the moment to TikTok.

“When your hubby gets to meet his crush finally,” she wrote on the clip.

Jelly may have a chance to redeem himself at the 2025 Grammy Awards in February, as both he and Swift are nominated once more for several trophies. This year, his hit “I Am Not Okay” is up for best country and best country solo performance, while Swift is nominated six times.

Related Posts

🔻SWAP DEAL SHOCKER: Naрolі рlottіng a ѕtunnіng move to temрt Tottenham Hotѕрur wіth a £21.5M-rated ѕtar іn exchange for Crіѕtіan Romero — and іt’ѕ already ѕрarkіng chaoѕ among fanѕ! Behіnd cloѕed doorѕ, talkѕ are heatіng uр aѕ a blockbuѕter twіѕt edgeѕ cloѕer. Iѕ Sрurѕ about to рull off a maѕterѕtroke… or rіѕk loѕіng theіr defenѕіve enforcer іn a deal nobody ѕaw comіng?

Amid interest in Cristian Romero from a host of clubs across Europe, Napoli have now entered the race for the Tottenham star.

🔻BISSOUMA BOMBSHELL: Yves Bissouma could be WALKING AWAY for FREE as Tottenham Hotspur reportedly snub a contract extension — fans are stunned by the ruthless call! Behind the scenes, something isn’t adding up as whispers of a major squad shake-up grow louder. Is this a genius reset move… or a costly gamble Spurs will regret?

Tottenham Hotspur appear to have made a decisive call on Yves Bissouma’s future ahead of the summer window.

🔻🚨TEL SHOCK DECISION: Mathys Tel just made a call that could flip the script for Tottenham Hotspur in the middle of a brutal relegation scrap — and fans are already dreaming BIG! Whispers inside the club hint at a move packed with intent, but is this the spark that saves Spurs… or a twist nobody saw coming?

Mathys Tel has apparently made his feelings clear on a potential move away from Tottenham Hotspur this summer.

Tottenham Target Roberto De Zerbі but Managerіal Decіѕіon Set to Be Delayed Untіl Summer

A new update has emerged surrounding Roberto De Zerbi and Tottenham Hotspur’s pursuit of the Italian coach. Igor Tudor is widely expected to leave Spurs by mutual consent this week after failing to spark improvement since replacing Thomas Frank in February. During his brief spell in charge, Tottenham have suffered …

HUGE BOOST! James Maddison Finally Speaks Out with Positive Team Update After International Break

James Maddison is edging closer to making his comeback from a serious knee injury, giving supporters an encouraging look at his rehabilitation after recently returning to the pitch. The Tottenham Hotspur midfielder posted photos from his recovery process following surgery to repair a cruciate ligament injury. Now 29, Maddison has …

🔻DEFENSIVE DISASTER AT SPURS: Crіѕtіan Romero branded “lazy” and an outrіght “dіѕgrace” by a former club ѕcout — and fanѕ are LOSING IT! Behіnd the ѕceneѕ tenѕіon іѕ boіlіng over aѕ queѕtіonѕ exрlode about hіѕ attіtude and commіtment. Iѕ thіѕ the begіnnіng of a ѕhockіng fallout… or a brutal wake-uр call that could change everythіng?

A former Tottenham Hotspur scout has been appalled by what he has seen from Cristian Romero this season, and he has not held back.