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Jerritt Clark/GC Images JoJo Siwa and Kylie Prew
"Right person, wrong time," Siwa said of their split afterward, citing their age as a contributing factor. "We're both so young, she's 17, I'm 18, and we are literally best friends."
Just a few months later, the pair seemed to hint at reconciliation, with Siwa telling Extra that she was "very much in love" during an April 2022 interview. A few weeks and a joint trip to Disney World later, she officially confirmed on Instagram that they were back on.
From how they met to why they split and what they're doing differently this time around, here's everything to know about JoJo Siwa and Kylie Prew's relationship.
2020: JoJo Siwa and Kylie Prew meet on a cruise
In a rare Hollywood meet-cute, the pair first connected by chance on a cruise ship. There, they quickly developed a bond that initially started out as a close friendship.
"I told her my whole spiel that I tell everyone when they ask me my life story," Siwa later told PEOPLE about their first encounter. "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."
December 25, 2020: JoJo Siwa and Kylie Prew take a trip to Universal Orlando together
Kylie Prew Instagram
Things turned romantic between the "best friends" during a trip with Siwa's family to Universal Orlando over the holidays in 2020. The pair posed for photos together in coordinating holiday-themed onesies, with Prew dressed as The Grinch and Siwa as his dog, Max.
Siwa later told PEOPLE, "I fell in love with somebody who I didn't ever expect to fall in love with. We met on a cruise ship, she was my best friend. And then we went to [Orlando] together and all of a sudden ... it kind of all happened."
She added, "At the end of the trip she told me she was jealous of whoever my crush was. And I was like, 'Ha! You don't need to be, because it's you.' And we just both had this moment of 'Woah, okay so what I've been feeling is what you've been feeling.' It was really cool. It was a beautiful moment."
January 8, 2021: JoJo Siwa and Kylie Prew start dating
The pair officially began dating on Jan. 8, 2021, although Siwa would not share the news with fans until a month later.
"After being my best friend for over a year, January 8th 2021 I got to start calling this exceptional human my Girlfriend… and Since then I've been the happiest I have ever been!" she announced on Instagram in early February.
January 23, 2021: JoJo Siwa comes out as LGBTQ
Siwa came out as LGBTQ in January on social media, sharing a TikTok of herself lip-syncing Lady Gaga's "Born This Way" after spending a day with TikTok collective Pride House L.A. In response to the resulting speculation from fans about her sexuality, Siwa confirmed it by posting a photo in a T-shirt that read "Best Gay Cousin Ever."
The following day, Siwa addressed her fans on Instagram Live, telling them, "Personally I have never, ever, ever been this happy before and it feels really awesome. I've been happy for a little bit now. It's just so, so, so awesome."
When asked what "label" she identifies as, she replied that she wasn't exactly sure. "Right now what matters is that you guys know that no matter who you love, that it's okay. It's awesome and the world is there for you. There are so many people that are there for you," she told her fans. "I know everyone's situation is different and it might be harder for some people and easier for some people to come out or be themselves but I think coming out has this stigma around it — that it's this really, really scary thing, but it's not anymore. There are so many accepting and loving people out there that it's okay."
February 4, 2021: JoJo Siwa says she has the "most beautiful girlfriend in the whole world"
Before revealing Prew's identity, Siwa confirmed that she was in fact dating someone. "I do have the most amazing, wonderful, perfect, most beautiful girlfriend in the whole world. It's not something I'm ashamed of, I just haven't shown the internet yet," Siwa revealed on The Tonight Show.
She told host Jimmy Fallon that her girlfriend was "super encouraging" about her confirming her sexuality online and helped motivate her to do so.
She added: "About 10 minutes before I came out to do this interview today, I was again on the phone with my girl and I started crying. She's like, 'What's wrong with you?' And I was like, 'I'm just so happy because now I get to share what makes me the happiest with the world, and it makes my heart so happy.' "
February 8, 2021: JoJo Siwa goes public with her relationship with Kylie Prew
Jo Jo Siwa Instagram
The social media star made her relationship Instagram and TikTok official by revealing her girlfriend's identity to celebrate their one-month anniversary.
"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☁️," Siwa captioned a video of the new couple cuddling on TikTok.
"She seriously is the most loving, supportive, happiest, protective, and just the most beautiful perfect person in the world. And I get to call her mine! Happy one month to my girl! I love you more and more everyday [sic]!" she wrote alongside a trio of photos of the pair on Instagram.
February 14, 2020: JoJo Siwa and Kylie Prew celebrate their first Valentine's Day together
Siwa marked her first time celebrating the romantic holiday with a series of photos and videos of herself with her new love. "It's my first valentines dayyyy!!," Siwa wrote. "No one in the world makes me as happy as this girl does. I'm so thankful to have fallen in love with the most perfect person ever who makes me smile 24/7."
"I love you more than you'll ever know! ❤️," she added.
Prew shared photos of Siwa on her Instagram Story as well, along with the caption, "Getting to spend Valentine's Day with the BEST human on Earth."
April 7, 2021: JoJo Siwa jokes that she is "Ky-sexual"
Wil R/Star Max/GC Images
In a cover interview with PEOPLE about her coming out, Siwa joked that she still didn't know what "label" to use to describe her sexuality. "I still don't know what I am. It's like, I want to figure it out. And I have this joke. [My girlfriend's] name is Kylie. And so I say that I'm Ky-sexual," she said. "But like, I don't know, bisexual, pansexual, queer, lesbian, gay, straight. I always just say gay because it just kind of covers it or queer because I think the keyword is cool."
"I like queer," she continued. "Technically I would say that I am pansexual because that's how I have always been my whole life is just like, my human is my human."
April 2021: JoJo Siwa continues to rave about her love for Kylie Prew
Jo Jo Siwa Instagram
Throughout the month of April, Siwa took every opportunity to share how happy her new love made her. While presenting at the GLAAD Media Awards on April 8, she shared, "I have the best, most amazing, wonderful girlfriend in the entire world who makes me so, so, so happy. That is all that matters."
On Instagram, she shared clips of her and Prew twinning in various matching outfits during a trip to Disney World in Florida. "I love you to infinity and beyond:)❤️🚀," Siwa captioned a photo of them embracing in matching Buzz Lightyear masks.
At the end of their trip, Siwa shared a tearful selfie of herself along with the words "I. Don't. Like. Saying. Goodbye." She added that she cried every time the pair had to go their separate ways. "I wish we didn't have to, ever. But we do, and it just makes when we say hi to each other even more special."
"I'm going to go keep doing this [crying] for a lot longer," she said on her Instagram Story, adding that it's "the reality of long-distance. It's very, very, very hard, but it's the most worth it ever."
June 8, 2021: JoJo Siwa and Kylie Prew celebrate their five-month anniversary
In honor of five months together, Siwa shared a sweet tribute to her love on her Instagram Stories. "You've changed my life for forever," she wrote.
"I love you more and more every day," she continued alongside a snap of the couple embracing. "Thank you for being the best girlfriend in the world."
August 24, 2021: Kylie Prew shares her relationship advice: "Don't hold grudges"
The pair appeared on Siwa's mom's podcast, Success with Jess, to discuss their advice for navigating arguments in a relationship.
"This is going to sound stupid but don't hold grudges over stupid things because it's dumb and it's going to waste your time," Prew said. "It's not going to matter in an hour, it shouldn't matter then. So it's like, just let it go."
Siwa added, "No matter what, never go to sleep mad. Never go to sleep mad. Always end with an 'I love you.' Always end with an 'I'm frustrated but tomorrow it won't matter.' "
September 3, 2021: JoJo Siwa and Kylie Prew make their red carpet debut
The event marked the pair's first-ever official public appearance together, which saw them share a sweet smooch for the cameras.
September 15, 2021: JoJo Siwa shares that she and Kylie Prew celebrate four anniversaries each month
Jo Jo Siwa Instagram
The Dancing with the Stars runner-up revealed during an appearance on The Tonight Show that she and Prew "celebrate four days" each month: "When Ky asked me to be [her] girlfriend, when I asked Ky to be [my] girlfriend, when we told each other that we liked each other and when we kissed for the first time. So we celebrate all four: 8th, 14th, 28th, and 29th."
November 2, 2021: JoJo Siwa reveals she and Kylie Prew have split
"I have yet to talk about this officially, publicly, but we broke up," Siwa said. "But she is literally still my best friend. I talked to her yesterday, she just got a new puppy. She's awesome. She's having the time of her life, I'm having the time of my life."
She added that she felt "really lucky that I didn't lose her completely because, you know, even though relationships end, friendships don't have to end."
November 19, 2021: JoJo Siwa says she's not dating but is open to love again
In the wake of her split, Siwa told PEOPLE, "I haven't started dating at all, anybody, but whatever happens happens." She added that falling in love with Prew had happened so unexpectedly, saying, "And so I think I learned to just trust life and whatever's supposed to happen is going to happen."
Relationships aside, Siwa revealed, "I want to have a cuddle date. So if anybody out there needs a cuddle date, cuddle buddy, I'll take it."
November 21, 2021: JoJo Siwa reveals she and Kylie Prew "aren't as close"
While walking the red carpet at the American Music Awards, Siwa gave PEOPLE an update on where things stood at the time between her and Prew. "I was with my girlfriend for nine months. And those nine months were amazing and incredible. And obviously, I've talked about [it], we broke up. And one thing that I'm grateful for is that we're both okay," the entertainer said. "We obviously aren't as close as we used to be, but we're both okay. And we're both happy, and that's all that matters."
March 31, 2022: JoJo Siwa reveals she's in a new relationship
The "Boomerang" singer revealed that she was newly seeing someone during an appearance on the Rachel Uncensored podcast, sharing that she was "happy" and that the relationship was "exclusive."
"We're not single," Siwa said. "I say 'we're' because it's me and my multiple personalities within myself. … I am not single and I don't want to mingle. No, I'm a loyal lady."
Siwa didn't disclose her new partner at the time, although fans speculated it was Katie Mills, who she was spotted with in December 2021.
April 26, 2022: JoJo Siwa hints that she and Kylie Prew may have reconciled
In an interview with Extra, Siwa shared new details about her relationship, noting that she was "very much in love" and "really lucky that I'm loved unconditionally, too, by this human, and she is awesome."
She further fueled speculation that she and Prew were back together, noting her new relationship was also long-distance.
Addressing whether she and Prew had reconciled, Siwa replied, "I'm not saying yes or no … I should have told her I was doing press today and asked her what she wanted me to say."
May 1, 2022: JoJo Siwa and Kylie Prew return to Disney World
Before publicly acknowledging that they were officially back together, Siwa and Prew were spotted holding hands during a visit to Disney World with Siwa's dad, Tom, who shared snaps of the trio on Instagram.
May 5, 2022: JoJo Siwa and Kylie Prew confirm they are back together
Jo Jo Siwa Instagram
The couple revealed they were officially back together with a sweet photo of them sharing a kiss during their trip to Disney World in Orlando, Florida.
"If you love something let it go, if it comes back….🤍♾," Siwa captioned the post.
June 29, 2022: JoJo Siwa says it's "really nice" to be back together with Kylie Prew
Jo Jo Siwa Instagram
Speaking to PEOPLE about the pair's reconciliation, Siwa said that it felt "really nice," adding, "It's good to have people that have your best interest around you, and she really does have mine."
This time around, the pair are adjusting their boundaries as they go in order to make things work, said Siwa. "We're still learning things, setting new boundaries, releasing boundaries ... all the normal things."