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JoJo Siwa is still in her early 20s, but it feels like she’s lived a million lives already. In recent days, the former reality TV star has discussed a potential engagement with her current boyfriend, Chris Hughes, and updated her name to Joelle to reflect her ever-changing persona. While Siwa seems really happy with her life and relationship, things haven’t always been great in the love department. She’s had some pretty dramatic relationships. Let’s take a look back at everyone she has dated.

Siwa dated a teen she met on social media, and a girl she met on a cruise

JoJo Siwa was just a kid when fans met her on Dance Moms. Years later, her romantic life would become tabloid fodder. Siwa first made headlines in 2020 at just 17 when she confirmed a relationship with Mark Bontempo. The duo reportedly met on social media, and while they hit it off initially, the romance didn’t last. They confirmed their split just months later.

Siwa later came out and then debuted her relationship with Kylie Prew. According to People, Prew and Siwa started out as “just friends” after meeting on a family cruise. They grew closer, and by January 2021, they were officially dating. By November, the romance seemed to be over, but they reconnected in 2022 before calling it off for good. Siwa once referred to Prew as her first real love.

JoJo Siwa’s romance with Avery Cyrus led to an epic meltdown

After ending things with Prew for good, Siwa moved on to Avery Cyrus, a content creator. The pair met via TikTok in 2022, and things started off innocently enough. They filmed a bunch of couples’ content, and their relationship went viral, but the drama began pretty quickly. Within months of making things official, the duo split, and allegations of clout-chasing followed.

JoJo Siwa claimed Cyrus had “played her” in a dramatic social media post. In the years since the split, they have remained mostly quiet about each other, though they’ve been subtly shady over the years. Cyrus often mentions a controlling ex in social media uploads, but never names any names. Fans often suspect she’s referring to Siwa.

Her relationship with Kath Ebbs unraveled next

Before JoJo Siwa fell for Chris Hughes, she was dating Kath Ebbs. Well, technically, Siwa was dating Kath Ebbs when she fell for Hughes. Siwa and the Australian influencer began dating in late 2024, making it Instagram official in January 2025. Their romance was interrupted when Siwa filmed Celebrity Big Brother UK relatively early in the relationship.  

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While the pair were together, Hughes’ introduction into Siwa’s life changed everything. Ebbs and Siwa confirmed their split in April 2025. While Siwa insists Hughes had nothing to do with it, Ebbs tells a different story. They said they flew in to see Siwa at her wrap party, but were brutally rebuffed. Siwa broke up with Ebbs on the spot, leaving them reeling. Two months later, Siwa confirmed her romance with Hughes.