A Complete Timeline of JoJo Siwa & Kylie Prew's Relationship

JoJo and Kylie’s relationship history is complicated.

JoJo Siwa has had quite an eventful journey since turning 18 years old and coming out as gay to the entire world. Nonetheless, her career has only grown since coming out and living in her truth.

In the last few years, Siwa has competed on TV shows such as The Masked Singer season three, Dancing With the Stars season 30, and Celebrity Family Feud. She also became a judge on So You Think You Can Dance season 17, made an appearance on America’s Got Talent, and landed a recurring role on season three of High School Musical: The Musical: The Series. And starred in her own reality series Jojo Goes on Facebook. On the big screen, Siwa was featured as a voice actor in The Angry Birds Movie 2 and headlined the film The J Team.

In the meantime, the young multihyphenate has released three studio albums: 2018’s D.R.E.A.M. The Music, 2019’s Celebrate, and 2020’s JoJo’s Rockin’ Christmas. In 2020, she was named one of the 100 most influential people in the world according to Time Magazine. Then, in 2021, Fast Company named included Siwa in the publication’s prestigious “Queer 50” list.

And yet, despite being attached to so many different projects and launching new ones, Siwa has found time for love. Since her big coming-out moment, Siwa has been known for dating the same person: Kylie Prew. Alas, their relationship has involved quite a bit of back-and-forth that has left fans feeling rather confused.

JoJo and Kylie meet on a cruise in 2020.

According to People, Siwa and Prew met on a cruise ship back in 2020. From the moment they met each other, the popstar knew that there was something special about Prew.

“I told her my whole spiel that I tell everyone when they ask me my life story,” Siwa recalled. “She goes, ‘I could have Googled that. I want to know your life story. You just told me about your career. I want to know about you.’ And I was like, ‘No one’s ever asked me that before.’”

JoJo comes out in January 2021.

In January 2021, Siwa came out to the world in a rather unusual way: she shared a picture of herself wearing a t-shirt that read, “Best. Gay. Cousin. Ever.” Siwa wrote in the caption: “My cousin got me a new shirt.”

While many people and media outlets understood this as Siwa coming out of the closet, there were certainly those who didn’t exactly understand it at first.

They officially announce their relationship in February 2021.

Despite meeting in 2020 and traveling together in subsequent months, Siwa and Prew didn’t make their relationship official until February 2021. The popstar wrote in an Instagram post, “I did it!! My human. It’s been 1 month since my best friend asked me to be her girlfriend, and it’s been the best month ever. I love you.”

In later interviews, Siwa clarified that she and Prew had been best friends for a long time and started dating in January 2021. That explains why her Instagram announcement celebrated their first-month anniversary and why she referred to Prew as her “best friend” before they started to date.

JoJo and Kylie break up in November 2021.

After many months of nothing but happy posts regarding their relationship, Siwa and Prew reportedly broke up in November 2021. This was around the same when Siwa started to compete on Dancing With the Stars and made history for having a same-sex partner in the competition.

With so much going on surrounding her time on DWTS, Siwa didn’t elaborate too much on what happened for her relationship with Prew to end so abruptly. However, she did note during an interview with Paris Hilton in the This Is Paris podcast that Prew was the “right person [at the] wrong time.”

JoJo reveals that she’s in a new relationship in March 2022.

In March 2022, Siwa updated her fans that she was in a new relationship. On one hand, it was widely speculated that the popstar had a new girlfriend. On the other hand, certain fans felt like this was just Siwa’s way of re-introducing Prew into her life.

Kylie and JoJo officially get back together in May 2022.

Just two months after announcing that she had a “new girlfriend,” Siwa officially got back together with Prew. To celebrate this moment, Siwa shared adorable pictures with Prew in front of the Magic Kingdom castle at the Walt Disney World.

Given that their breakup had just been publicized in November 2021, this split felt more like a six-month hiatus for the couple than an actual termination of their relationship. In any event, a lot of fans were happy to see them back together.

JoJo and Kylie break up (again) in August 2022.

Unfortunately, the “second season” in Siwa and Prew’s relationship didn’t last very long, as the couple reportedly broke up once again in August 2022. Just like the first time, this new breakup felt like it came out of nowhere given that the couple had been sharing nothing but love and future plans with one another in recent months. Nonetheless, Page Six reported that both Siwa and Prew confirmed their breakup via social media.

“I don’t like drama and it makes me really, really anxious,” Prew said on social media. “So, I don’t want to talk about it for a while, but, um, someone asked me just now if I was single [and] I am.” She added, “I’ve been single for almost two months and it’s okay. It’s not deep, I promise. Everything’s fine.”

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