Taylor Swift and Travis Kelce have enjoyed plenty of time together while Swift rests following her historic Eras Tour and Kelce licks his wounds following the Kansas City Chiefs‘ Super Bowl loss and preps for next season. The two haven’t been out and about together as often, but that could change soon, according to a new report.

In fact, Swift could join Kelce at one of the tight end’s favorite events in May

The Kentucky Derby is an annual, and beloved, stakes race that takes place at Churchill Downs in Louisville, Kentucky. “The modern Kentucky Derby is traditionally held on the first Saturday in May (with two notable exceptions: for World War II, when it was held in June, and during the global pandemic of 2020, when it was held in September),” notes Go to Louisville.

The 2025 edition of the Kentucky Derby is set to take place on Saturday, May 3.

The outlet Deuxmoi, according to an April 12 report, has learned exclusively that Kelce “has allegedly inquired about renting a full box for the prestigious event.” They add that, “The box in question reportedly accommodates six people, immediately sparking questions about who might fill those coveted spots.”

So, could Swift be filling one of those spots? Well, it would be difficult to see her skip this event if Kelce does end up making such a big box seat purchase.

Deuxmoi adds that while Kelce “has been known to enjoy the Derby festivities in the past – he was spotted looking dapper at last year’s race, even celebrating a winning bet – the potential addition of Taylor Swift would undoubtedly elevate the celebrity wattage to a whole new level.”

Fans may remember that last year, Kelce was at the event, but Swift was not, because she was prepping for her Eras Tour, which was hitting Paris, France, a few days after the Derby. This year, of course, Swift doesn’t have the Eras Tour, so that, in theory, opens her up for events such as these.

“The image of Taylor in a stunning Derby hat, perhaps coordinating with Travis’s undoubtedly stylish ensemble, is enough to set social media ablaze,” Deuxmoi notes.

So, there is certainly talk about the possibility of Swift and Kelce attending the Derby together for the first time ever. “Whether or not Taylor Swift and Travis Kelce make their Derby debut as a couple this year remains to be seen,” Deuxmoi states. “But one thing is for sure: all eyes will be on the VIP boxes come May 3rd, with fans eagerly hoping for a glimpse of their favorite power couple amidst the Derby Day excitement.”

If Swift does attend with Kelce, it will be something of a next step, especially since the two have been staying out of the public eye more lately. If this couple were to come out from their safe haven for anything, the Derby, which has been a mainstay since 1875, would make for an apt reason.