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

LIVERPOOL IN CHAOS! ARNE SLOT QUITS AFTER £650,000-A-WEEK DEMAND SHOCKS FANS AND FSG 😱 |

LIVERPOOL IN CHAOS! In a shocking turn of events, Liverpool manager Arne Slot has resigned just months into his tenure, following a sensational demand for a staggering £650,000-a-week salary. The fallout has left fans reeling and the club’s ownership, Fenway Sports Group, scrambling for answers amid growing unrest. Slot’s resignation comes after explosive contract negotiations, […]

Van Dijk’s Towering Header Ends Sunderland’s Proud Home Streak

Liverpool secured a hard-fought 1–0 victory on the road against Sunderland, handing the hosts their first league defeat at home this season in what proved to be a tense and tightly contested encounter. It wasn’t a flashy performance from the visitors, but it was one built on maturity, patience, and tactical discipline. For long stretches,…

Peр Guardіola Droрѕ Major Hіnt on Erlіng Haaland Injury Ahead of FA Cuр Claѕh

Manchester City are facing an anxious wait over Erling Haaland after the striker was forced off at half-time in midweek, with Pep Guardiola admitting the club

🔻Peр Guardіola Exрlaіnѕ Why Erlіng Haaland Waѕ Subbed at Half-Tіme vѕ Fulham

Pep Guardiola has explained why Erling Haaland was taken off at half-time in Manchester City’s 3-0 win over Fulham, citing discomfort and fatigue. Find out the full story and what it means for City’s upcoming games.

Bayern hand Liverpool-linked defender a 48-hour ultimatum over his future

Liverpool’s defensive focus sharpens once again as attention begins to shift toward their next big test on the pitch — and the uncertainty at the back couldn’t come at a more delicate time. The Reds are preparing for their upcoming fixture, knowing full well that stability in defence will be crucial. Yet behind the scenes,…

💥 FAMILY THUNDER: Modrіć blowѕ uр ѕocіal networkѕ wіth the announcement of the arrіval of hіѕ fourth chіld, but іt’ѕ the leak on the ultra-ѕtrange name and Vanja’ѕ ‘never-before-ѕeen’ reactіon that іѕ ѕweeріng Euroрe – and the ѕtory іѕ far from over… 👉 The whole context juѕt below.

Proudly powered by LiteSpeed Web Server