Taylor Swift's Praising Diddy Has Everyone Giving Side Eyes — Years Later

In a now resurfaced video, Taylor Swift sang the disgraced Hip-Hop mogul's praises

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Taylor Swift and Diddy at the 2023 MTV Video Music Awards in Newark
Taylor Swift and Diddy at the 2023 MTV Video Music Awards in Newark
Photo: Getty Images (Getty Images)

As the hole for Sean “Diddy” Combs keeps getting deeper and deeper, many are scavenging the internet and coming up with anything which possibly hinted at Diddy’s current spew of allegations. This time, America’s Sweetheart is getting wrapped up in the Diddy debacle after a video clip from 2011 is coming back to life.

The resurfaced video of superstar Taylor Swift is shaking the internet. In the 2011 video, then 21-year-old Swift sat down with one of America’s favorite chefs, Rachael Ray, for an interview. During a segment of Ray’s show, Swift was asked a series of rapid fire questions all about celebrities, like Hollywood favs Madonna, Lady Gaga, and— you guessed it— P. Diddy.

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When asked “Who would you have taken to the prom?” The “Shake It Off” singer said “it would be a fun group.” She then proceeded to hold up photos of Katy Perry, Jennifer Lopez, Justin Timberlake, Sheryl Crow, and the disgraced mogul, saying they would all make great prom dates for her. In response, Ray said “you’re going on a freaky prom date” in obvious jest, but 13 years later, who would’ve known her joke would age so terribly.

Taylor Swift once said Sean ‘Diddy’ Combs would be one of her dream prom dates

Swift gave her reasons for choosing the five celebrities. She named J. Lo as a great dancer, Perry because she would “just be so much fun,” and she went on to say Crow is “really down-to-earth and really cool.”

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As far as Diddy goes, the pop/country star simply said “Diddy’s really always been very nice to me.” She added, “He would be fun to be in the prom group.” Ray, to the same effect, agreed with Swift saying “He’s a gentleman, isn’t he?” She continued, “He’s a lovely gentleman.”

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On social media, Swift has been catching heat over her “prom date” comments. People are calling her anything from a “devil worshipper” to “she-Diddy.” One TikTok user, @kaitlincarter93, wrote in defense of Swift saying “She was like 17 here. Y’all need to chill out 😂 she had no idea what he was about then.” She continued, “This going around in this context is probably her worst fear bc shes called out the ppl who are like him.”

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On X, @KristoCherubim said Swift is either “super ignorant and blue-eyed” or she’s “in on it” — it being Diddy’s alleged secrets.

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Another X user said “Hold her accountable for what she has said in the past. People drag other celebrities for what they have said. She is not an exception.”

Swift and Combs have had a seemingly cordial relationship over the years. At the infamous 2009 MTV Video Music Awards— you know, the one where Kanye stormed the stage and took the mic from Swift— the country star and Diddy snapped a few pics together. In 2023, they were spotted together again at that year’s MTV Awards, but other than that, there’s no real evidence suggesting Swift is tied to Combs in any alarming way.

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2009 MTV Awards
2009 MTV Awards
Photo: Getty Images (Getty Images)

Since abuse allegations against Combs first erupted in 2023, Swift hasn’t said a word publicly on the matter. For very obvious reasons, it seems Swift is keeping quiet, but we all know staying silent won’t stop the internet from trying to incriminate you, even if they have to pull up a video from 13 years ago.

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Combs was arrested by the FBI in September and charged with sex trafficking, racketeering and transportation to engage in prostitution. He remains in jail after being denied bail. The trial is set for May 2025.