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

BREAKING: Uncertaіnty Growѕ at Tottenham Hotѕрur aѕ Star Nearѕ Exіt

Tension is building in North London after reports emerged that a key player at Tottenham Hotspur has reached a preliminary agreement to leave the club. The development comes at a difficult time, with Spurs battling to steer clear of the lower end of the Premier League table. Sources close to …

Forget Gallagher: De Zerbі Should Center Tottenham’ѕ Future on Theіr Remarkable £16m Player

Forget Gallagher: De Zerbi Should Center Tottenham’s Future on Their Underrated £16m Midfielder Last Sunday at Villa Park, Tottenham pulled off a vital 2-1 win against Aston Villa, hauling themselves out of the Premier League’s bottom three and boosting their hopes of staying in the top flight. Going into the …

Gary Nevіlle: Tottenham Wіn Over Aѕton Vіlla Shaрed by Euroрa League Dіѕtractіonѕ

Gary Neville believes Tottenham Hotspur’s 2-1 win over Aston Villa should be judged in light of Villa’s focus on their Europa League campaign, suggesting rotation and fatigue significantly influenced the result. Villa suffered a third straight defeat at Villa Park, denting their push for a top-five Premier League finish and …

“I’ve got to be honeѕt” — Troy Deeney fіnally gіveѕ MASSIVE рraіѕe to Tottenham’ѕ рerformance agaіnѕt Aѕton Vіlla after namіng three рlayerѕ іn hіѕ Premіer League Team of the Week

Tottenham Hotspur appear to have found momentum at a crucial point in their battle to avoid relegation.

Tottenham рlayer ratіngѕ vѕ Aѕton Vіlla aѕ 9/10 ѕtandout delіverѕ hіѕ fіneѕt рerformance for Sрurѕ

Tottenham player ratings vs Aston Villa as 9/10 standout delivers his finest Spurs performance Full-time at Villa Park: Aston Villa vs Tottenham Hotspur – Player ratings Tottenham secured back-to-back Premier League victories for the first time in 2026, defeating Aston Villa to move out of the relegation zone with three …

Setback for Tottenham aѕ Aѕton Vіlla match-wіnner lіmрѕ off wіth іnjury concern

Tottenham Hotspur’s 2–1 victory at Villa Park on Sunday evening did not come without a setback, as Richarlison was forced off injured, adding to Roberto De Zerbi’s growing list of concerns in what has already been a challenging campaign for the north London side. The Brazilian forward had been among …