Entertainment

Taylor Swift Once Dreamed of Prom with Diddy, Saying He Was ‘Always So Nice’.

More than ten years before the disgraced rapper was arrested for 𝓈ℯ𝓍 trafficking, Taylor Swift declared that Sean “Diddy” Combs would be one of her ideal prom dates.

A 2011 video that has since surfaced shows the singer of “Lover” playing a celebrity quiz game while making an appearance on the “Rachael Ray” show at the age of 21.

Taylor Swift once said Sean “Diddy” Combs would be one of her dream prom dates during a 2011 appearance on the “Rachael Ray” show. The Rachel Ray Show

The pop star held up pictures of other music icons, such as Combs, Jennifer Lopez, and Katy Perry, while she responded to a series of quick-fire questions.

The “Lover” songstress included the now-disgraced rapper in her answer while playing a celebrity quiz game.

When asked who she would have taken to prom, Swift, now 34, responded, “It would be a group, and it would be a really fun group.”

“Boy, you’re going on a freaky prom date,” Ray, now 56, quipped as the singer made her choices.

Seconds later, Swift held up pictures of Combs, Perry, Lopez, Justin Timberlake and Sheryl Crow.

She also chose Katy Perry, Jennifer Lopez, Justin Timberlake and Sheryl Crow.The Rachel Ray Show

The then-21-year-old singer had various music superstars to chose from for the game. The Rachel Ray Show

“Why that spectacular array of people?” the talk show host asked.

“Because … all these different reasons,” the “Fearless” hitmaker explained. “Well, Katy would just be so much fun. She’s just, like, crazy fun, like spontaneous.”

“Diddy’s really always been very nice to me,” Swift continued, adding, “He would be fun to be in the prom group.”

“He’s a gentleman, isn’t he? He’s a lovely gentleman,” Ray chimed in.

“Diddy’s really always been very nice to me,” the Grammy winner, seen here with Combs in 2009, explained at the time.

“He would be fun to be in the prom group,” Swift added.

Swift’s remarks made headlines after the moment was shared in a since-deleted TikTok video and several fans claimed the clip “didn’t age well.”

“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,” one person commented, per the Daily Mail.

“Back when we were so naive,” a second added, while a third wrote, “This aged like milk.”

Combs, 54, was arrested on Sept. 16 and charged with 𝓈ℯ𝓍 trafficking, racketeering and transportation to engage in prostitution.

Last month, Combs was arrested for 𝓈ℯ𝓍 trafficking.

He is currently behind bars in Brooklyn.

The founder of Bad Boy Records is charged with organizing “freak-offs,” where women were reportedly forced to engage in hours-long 𝓈ℯ𝓍 activities under duress. Combs is presently awaiting trial at the Brooklyn Metropolitan Detention Center after entering a not guilty plea to the accusations against him. He has insisted on his innocence and refuted every accusation of misconduct.

Related Posts

Drake Backs Down: Admits iHeartMedia Did Nothing Wrong in Settlement

Drake had accused iHeartMedia of accepting illegal payola payments from UMG to boost the radio airplay of Kendrick Lamar’s “Not Like Us” diss. One of the most unexpected developments in the Kendrick Lamar and Drake battle was that it evolved from a question of ‘Who won the battle?’ to ‘Who won the lawsuit?’ However, Drizzy has one less target on his list, as he settled a legal petition against iHeartMedia over the Kendrick diss track “Not Like Us.” Basically, he claimed back in November that Universal Music Group (UMG) made illegal payola payments to iHeart in order to artificially boost radio airplay for the West Coast banger. A court filing in Texas’ Bexar County confirmed this settlement, and an alleged iHeart source reportedly spoke to Rolling Stone on the matter. “In exchange for documents that showed iHeart did nothing wrong, Drake agreed to drop his petition. No payments were made – by either one of us,” the iHeartMedia source explained. The court documents did not specify this, however. “Petitioner and iHeartMedia, Inc. have reached an amicable resolution of the dispute to the satisfaction of both sides,” they read. “We are pleased that the parties were able to reach a settlement satisfactory to both sides and have no further comment on this matter,” the Toronto superstar’s team stated separately to iHeart’s comments. Why Is Drake Suing UMG? Despite this move, Drake is moving forward in his UMG lawsuit, specifically alleging that the label and distributor – which he and Kendrick are both under – engaged in defamatory practices. While K.Dot is not a defendant in this suit, the core of the argument specifically portrays his accusations of pedophilia against the OVO mogul as defamatory. The January filing accuses UMG of artificially boosting the track’s commercial performance and engaging in defamatory campaigns on social media through its promotion. Furthermore, UMG faces a March 16 deadline if they want to file a motion to dismiss. They already denied any and all of Drake’s claims. Through his since-settled iHeartMedia petition, he sought to orally depose iHeart corporate employees, and filed the petition to secure more factual information to determine whether to move forward with more accusations in addition to defamation. Aubrey Graham’s team is also calling UMG out for attempting to delay the case despite their ample time to prepare.

Tragedy Strikes: Rapper G Lil Ronnie’s Daughter Reportedly Killed

This is still a developing story, so details are scarce as of right now, but our thoughts go out to the loved ones of G$ Lil Ronnie. 2025…

Rick Ross Fires Back at Freeway Ricky Ross as Feud Escalates!

Rick Ross has responded to a shot taken at him by the man from whom he took his rap name, mocking “Freeway” Rick Ross as a “gangsta informant” in…

Wack 100 Warns Joe Budden: ‘Get Armed Security’ Amid 50 Cent Feud!

The 50 Cent and Joe Budden beef has entered a new level. A mysterious event in the strip club, prompted Budden to leave. Now, Wack 100 is offering commentary,…

Tory Lanez Fires Shots at PartyNextDoor in Leaked Diss Track Snippet!

Tory Lanez performs on stage at Prudential Center on September 13, 2019 in Newark, New Jersey. Manny Carabel/Getty Images Even though he’s behind bars, Tory Lanez has continued to escalate his boiling feud with fellow Toronto singer PARTYNEXTDOOR. While PND walked back his most recent diss and apologized to Lanez, Tory continued to follow up on Friday (Feb. 28), with a preview of a…

Aubrey O’Day Throws Subtle Shade at Diddy After ‘The Masked Singer’ Elimination!

Jailed Diddy has ‘hit back’ at former protegee Aubrey O’Day after her barbed remarks about him on The Masked Singer. O’Day, 41, shot to fame in Diddy’s girl…