A Look at Maddie Ziegler's Romances Over the Years

After meeting on the set of Dance Moms in 2016, Maddie and fellow performer Kenneth became close friends. In fact, they were so close that fans wondered if there was something more to their relationship. Dating rumors swirled after Maddie posted a photo with Kenneth, captioning it "Missed him," which prompted her younger sister Kenzie to comment, "OTP" (meaning "one true pair"). Some of Maddie's followers took that as a subtle hint that they were a couple, but Maddie never acknowledged the comment and the speculation fizzled out. Neither Maddie nor Kenneth ever confirmed or denied their supposed romance.

Maddie's most well-known relationship was with the Instagram personality Jack Kelly. The two started dating on Jan. 1, 2017, about six years after they initially crossed paths. "We met when we were like eight, and then years later we met again, and he's from Australia, so it was kind of funny — and now we're just dating," Maddie told Galore in September 2017.

Throughout the course of their relationship, Maddie and Jack shared a ton of heartwarming photos on social media. The Aussie even made a few appearances on Maddie's YouTube channel as they did couples yoga and a Q&A with fans.

But in August 2018, the duo called it quits. The long distance was reportedly one of the main reasons behind the breakup. After the split, Maddie unfollowed her former beau on Instagram, and Jack noticeably deleted photos of Maddie from his page and added "Good riddance" to his bio.

In October 2018, People confirmed that Maddie was dating Stevie Wonder's son Kailand Morris, shortly after he attended her Sweet 16 celebration. The two met on the set of Dancing With the Stars: Juniors when their younger siblings Kenzie and Mandla were on the show together.

They gave fans a few peeks into their relationship, sharing snaps from a trip to Disneyland and a night out at the Lancome x Vogue Holiday Event in November 2018. They also starred in a stunning portrait series by photographer Tyler Shields in January 2019. But after a while, the West Side Story star stopped sharing pictures with Kailand. She still follows him on Instagram, but it appears they are no longer dating.