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‘He’s a gentleman, isn’t he?’: A once-naive Taylor Swift saw Diddy as her perfect dream date, wanted to go on group prom with him and Jennifer Lopez

I bet the pop star wishes she could shake this off.

Diddy and Taylor Swift pose during the 2023 MTV Video Music Awards at Prudential Center
Photo by Catherine Powell/Getty Images for MTV

Footage has recently emerged of Taylor Swift praising the disgraced music star Sean “Diddy” Combs, formerly known as Puff Daddy and P. Diddy. Posted to social media by a fan of Swift, the clip shows singer answering host Rachel Ray’s quick-fire questions, including one about who she would take to prom.

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As part of a fun game, the country and pop superstar was asked by Ray on The Rachel Ray Show to pick a “perfect prom date” from a line-up of music greats. Swift went on to pick an entire group for her hypothetical prom date, naming everyone from Jennifer Lopez to Justin Timberlake, and Katy Perry, for reasons such as being “really funny” or “down-to-earth”.

Photo by Rob Verhorst/Redferns

This is a cute clip showcasing how Swift felt about her fellow music stars at the time of recording. Or it would be, if she hadn’t chosen a particular person. Unfortunately for the “Shake It Off” singer, one of her choices has gone on to be a lot less charming than she might have thought, and certainly not prom date material.

Swift, just 21 at the time of recording, picked Combs as part of her dream prom date group, citing his charm and the fact that he had “always been very nice to [her]” as reasons for his inclusion. Doubling down on a sentiment that has now aged like milk, Ray agreed with Swift’s assessment and called Combs “a lovely gentleman”.

Check out the clip below to see for yourself.

Although the comments, which were said in complete innocence, are likely to now embarrass Swift given the media furore around Combs, there’s no reason she should be dragged through the mud for her words. The comments simply show a young woman drawing from her limited personal experience with a fellow music star.

While Combs made a fortune as a rap star and producer in the 1990s, he has made headlines for far less savory reasons in recent months. Combs has been accused of multiple counts of rape, sexual assault, and assault among other crimes such as trafficking, with new allegations and rumors continually emerging.

Photo by Christopher Polk/Getty Images

There has even been a video of Combs attacking his former partner, Cassandra Ventura. Not only are these allegations serious and upsetting, the sheer volume of accusations is cause for major concern. BBC recently reported on seven new lawsuits against the embattled singer, adding to an increasingly massive pile of allegations and civil suits in progress. All of that on top of a federal indictment for the sex trafficking charge.

Combs, along with his legal team, have consistently asserted his innocence. Combs has been linked to numerous high profile crimes and events, including the abuse of his own personal trainer, longstanding rumors of his connection to the death of Tupac Shakur, and allegations that he poisoned Jamie Foxx.

Swift is fortunate in that her words are likely to be forgotten quickly enough. But the battle facing Combs is much more serious, and it’s incredibly unlikely to be forgotten any time soon given its scale and severity. Swift isn’t the only major pop star to have her name troublingly linked to Combs recently, with Beyoncé facing an onslaught of speculation around her association with the rapper, even though she has responded to such rumors with legal action.

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