Resurfaced interview of Taylor Swift picking Diddy as her ‘dream prom date’ just hasn’t aged well
Taylor Swift, the global pop icon known for her evocative songwriting and dynamic performances, has always been open about her personal life, often incorporating her experiences into her music. However, in a recently resurfaced interview with Rachel Ray, a young Swift revealed that her ultimate “dream prom date” was music mogul Sean “Diddy” Combs. Well, given the current status of the rapper who has been arrested on multiple charges of racketeering and sex trafficking, this has definitely raised eyebrows.
In 2011, Swift appeared on 'The Rachael Ray Show' and took part in 'Swift Decision', a game named after her. At just 21 years old, Swift found herself answering rapid-fire celebrity-themed questions. When asked, “Who would you have taken to prom?” she didn’t hesitate. Instead of picking just one date, she playfully held up multiple celebrity face paddles, revealing an unexpected mix of stars, including Diddy Combs, Katy Perry, Jennifer Lopez, Sheryl Crow, and Justin Timberlake. "It would be a group, and it would be a really fun group," Swift said enthusiastically. Ray couldn’t help but tease, “Boy, you’re going on a freaky prom date.” Swift also singled out Diddy, explaining, “He’s always been very nice to me. He would be fun to be in the prom group.” Agreeing, Ray added, “He’s a gentleman, isn’t he? He’s a lovely gentleman.”
Now, the clip has sparked renewed interest online, leading many fans to reflect on Diddy’s presence in Swift’s “prom group” in light of his legal situation. One person remarked under the YouTube video's comment section, "This aged like milk." Another said, "As a millennial, we looked up to these people. we didn’t know what was really going on. this is like fearless/speak now taylor. she like 19-21 here." "Oopsie," wrote one person. Another added, "This didn't age well lol." One individual wrote, "This aged horribly." Another pointed out, "Back when we were all so naive."
Swift has never been shy about revealing her celebrity crushes over the years. According to Live Journal, she once admitted in an interview with Your Prom magazine that she had a crush on 'Gossip Girl' star Chace Crawford. “I write songs about the things that happen to me because it helps me figure them out. Writing songs is like breathing for me,” she shared. A few years later, ScreenRant reported that Swift hinted at having a romantic interest in someone while discussing her song 'Mine' with Rolling Stone, revealing it was “inspired by a boy she liked at the time.”
Despite the resurfaced clip, Swift, now 35, remains focused on her present, and that includes her current relationship with NFL star Travis Kelce. Recently, Kelce and Swift enjoyed a cozy date night with Patrick and Brittany Mahomes ahead of the 2025 Super Bowl. The power couple was spotted dining at Lilette, an upscale French restaurant in New Orleans, sharing laughter and good food with their close friends. An insider revealed, "They seemed to be having a wonderful time, enjoying each other’s company and the exquisite cuisine, as reported by People.