9 Celebrities Who Went On Dates With Their Fans & Made Some Major Dreams Come True

It's a once-in-a-lifetime chance. Just you, your celebrity crush, and one magical, life-changing date night ahead of you. To most fans, this sounds like a dream they wouldn't want to wake up from, but for a select few, this has been reality. Just ask cancer survivor Kevin McGuire, who was Taylor Swift's plus-one to the Academy of Country Music Awards, or Cpl. Kelsey De Santis, who went to the Marine Corps Ball with Justin Timberlake. Some of these stories will melt your heart. Others will make you green with envy. But all of them sound like a dream come true!

Click through for the stories of nine celebs who took their fans on very special dates.

Taylor Swift

When cancer survivor and Taylor Swift superfan Kevin McGuire asked Swift to prom, she unfortunately could not make it to the dance. But the “Shake It Off” singer did invite McGuire to be her date for the Academy of Country Music Awards. When he could not make the show, she followed up by asking him to be her date in 2013, and they finally ended up meeting!



Before her bad gal days, RiRi went to prom with a super nervous fan of hers for MTV’s Once Upon A Prom in 2007. “I want to let you know how terrified I am,” the fan confessed to her. Luckily for him, Rihanna spent the night dancing away with the guy and his friends. They even took a prom photo together!


Mila Kunis

She made a lucky Marine’s dream come true back in 2011. After Marine Sgt. Scott Moore set up a YouTube page called Go With Me Mila to request that the actress accompany him to the Marine Corps Ball, the videos caught the attention of Justin Timberlake, who told her, “You need to do it for your country.” And she did! How patriotic.


Justin Timberlake

Making good on his word! Shortly after Timberlake convinced Kunis to go to the Marine Corps Ball after being invited via YouTube, another soldier was inspired to post an invite of her own — for Timberlake! Cpl. Kelsey De Santis invited him to a separate Marine Corps Ball, which the actor-singer graciously accepted.

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Dwyane Wade

The Heat basketball player gave a Miami teenager the surprise of a lifetime when he showed up to her prom after she invited him to be her date in a YouTube video. Though he did not reply to her message, she sent the exact location and information just in case. Smart move on her part!


Justin Bieber

In the midst of his ongoing rehabilitation of his image, the Biebs took a much deserving fan on a date to the Young Hollywood Awards in 2014. He went with Make-A-Wish recipient Grace Kesablak, much to the audience’s delight.


Tupac Shakur

Bet you didn’t see this one coming! The late, great rapper gave a superfan the surprise of her life after she wrote a letter to his fan club asking him to be her prom date. He showed up at her doorstep and not only offered to escort her to the dance, but also offered to purchase her dress and bring a limo. Tupac cares!

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Kristin Cavallari

The power of Twitter is undeniable. Without it, Cavallari would not have seen Lance Cpl. Jonathan Burkett’s invite to the 2011 Marine Corps Ball. Luckily, the digital age helped Burkett’s dream girl become his date for his big night! Luckily, Cavallari’s boyfriend was totally OK with it.


Jason Segel

When Chelsea Gill posted a silly song to YouTube asking Jason Segal on a date, she did not expect it to go viral. She also did not expect to receive a response. But that she did. And even better than that, the comedian-actor was so tickled by the video he asked her to be his date for the Chicago Film Critic Awards Show. Dreams do come true!