After some time apart, pop superstar Taylor Swift and NFL tight end Travis Kelce reunited for a romantic dinner Friday night, fueling speculation that an engagement may be on the horizon. The couple were seen dining at Harry’s Bar and Restaurant in West Palm Beach, just a short drive from Kelce’s new $20 million waterfront mansion in Boca Raton.
Luxury date night raises eyebrows
The pair arrived at the upscale eatery shortly after 10 p.m., reportedly sparing no expense with a meal that included Wagyu-style beef, lobster risotto, cacio e pepe, Dover sole, and more. Their indulgent order racked up a bill of more than $400, as per Daily Mail. The intimate dinner — which comes amid growing buzz about their relationship — has only intensified speculation about a future proposal. “Everyone is just waiting for Travis to ask her parents for her hand in marriage,” a source close to the couple shared. “Her parents will say yes, and they can’t wait for them to get engaged.”
Engagement timeline: Post-NFL career in sight?
Although nothing is reportedly imminent, insiders say an engagement is inevitable. “It will 100 percent happen,” the source confirmed. “Taylor and Travis are treating this relationship as their last — when they get engaged, married, and start a family, it will be exactly when it is meant to happen.” A major clue to the timing? Kelce, 35, is currently in the NFL off-season, with many expecting the 2025 season to be his last. According to sources, the engagement conversation will likely take center stage once his playing days are over. Some insiders are now pointing to Super Bowl 2026 as a potential milestone for both his retirement and a life-changing proposal.
In recent months, Swift and Kelce have been spending more time with each other’s families — a sign that their bond is deepening. Earlier this month, they celebrated Mother’s Day together in Philadelphia with both sets of parents, joined by Kelce’s brother Jason and sister-in-law Kylie. Kelce has also been enjoying quality time with his father, Ed Kelce, at his Boca Raton estate, which features six bedrooms, a home cinema, a waterfall-edge pool, and a private dock. “Taylor is impressed with Travis in so many ways, especially how he treats her parents and his own,” said a source. “She knows that when they start a family, he’ll be the kind of father who puts in the work.”
Taylor Swift keeps low profile amid Blake Lively rift
Swift has reportedly been keeping a low profile recently due to a strained friendship with Blake Lively. The pop icon was briefly pulled into Lively’s legal battle with actor Justin Baldoni when Baldoni’s legal team subpoenaed Swift as a witness — a move later reversed after they allegedly obtained evidence from Swift’s father, Scott.
Through it all, Kelce has remained a steady presence. He even unfollowed Lively’s husband, Ryan Reynolds, on Instagram in what many viewed as a show of loyalty to Swift.