The 34-year-old football star made an appearance at the Big Slick Celebrity Weekend in Kansas City, Missouri, a charity event supporting Children’s Mercy Hospital. Sudeikis, in a lighthearted moment, prodded Kelce about his intentions towards his pop star girlfriend, Taylor Swift, asking when he planned to propose and suggesting Swift didn’t need to work anymore. Kelce, sporting a smile, tactfully avoided a direct response.
Kelce and Swift are believed to have commenced their relationship in July 2023, with Swift making her first public appearance supporting Kelce at one of his football games in September. Reflecting on the early stages of their romance, Swift disclosed that they spent ample time together privately before stepping into the public eye. 
Regarding their first public outing together, Swift clarified that it wasn’t a formal “first date,” but rather a natural progression of their relationship. She emphasized their support for each other in public settings and dismissed any notions of a secretive relationship, stating they were simply proud of each other.