SUMMARY
  • Taylor Swift chose Diddy as her dream prom date on TV.
  • She created an epic squad with stars like Katy Perry and J.Lo.
  • The singer praised Diddy for being nice and fun to be around.

Let’s take a trip back to 2011 when a 21-year-old Taylor Swift appeared on the Rachael Ray show. She was playing a fun game about celebrity crushes, and guess who she wanted to take to prom? That’s right—Sean “Diddy” Combs!

Taylor Swift in I Bet You Think About Me
Taylor Swift in I Bet You Think About Me (Credits: YouTube/Taylor Swift)

In the clip that’s making waves online again, Tay is asked to pick her dream prom date from a group of famous faces. With her hair on point and her smile shining, she surprised everyone by saying Diddy is on her list. But there’s a reason behind her choice!

1. Do Taylor Swift and Diddy Know Each Other?

Taylor Swift in Bad Blood
Taylor Swift in Bad Blood (Credits: YouTube/Taylor Swift)

Taylor Swift and Sean “Diddy” Combs have appeared in several photos together, showing they know each other. Their social media posts also hint at a friendly connection. However, they have never collaborated in music.

2. Why Did Taylor Swift Choose Diddy For Prom?

Diddy
Diddy (Credits: X/@diddy)

Let’s rewind to that memorable moment on the Rachael Ray show. When asked who she would take to prom, Swift didn’t just choose one person—she created a whole squad! Along with Diddy, she picked Katy Perry, Jennifer Lopez, Justin Timberlake, and Sheryl Crow.

So, why did she choose Diddy? T-Swizzle said:

Diddy’s really always been very nice to me. He would be fun to be in the prom group.

That’s a sweet compliment! It shows that Diddy made a good impression on her. Ray even called him a “lovely gentleman.” However, the clip is particularly making waves online again in light of the rapper’s recent s*x scandal.

3. Taylor Swift’s Prom Squad That Could Have Been

Now, let’s talk about Swift’s dream prom squad. To answer the question, the songstress held up photos of Sean Diddy Combs, Katy Perry, Jennifer Lopez, Justin Timberlake, and Sheryl Crow, calling them her ultimate dream prom squad.

She wanted a blend of fun personalities. Swift said Perry would be great because she’s “crazy fun and spontaneous.” Who wouldn’t want someone like her to keep the energy up?

Katy Perry in Birthday
Katy Perry in Birthday (Credits: YouTube/Katy Perry)

Then there’s J.Lo, who brings the glamour, and Timberlake, the heartthrob. Crow adds some classic rock flair. This crew would be like a mini music festival! Young Swifty clearly knew how to create a good time, even if it’s just in her imagination.

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