Photo: Enos Solomon/FilmMagic ; Gregg DeGuire/WireImage

Nick Cannonis known for his blended family.
Though the rapper has previously said he has “failed miserably” so many times at monogamy and relationships," Cannon hasn’t ruled out another trip down the aisle.
“I’m a hopeless romantic at the end of the day, so I love the concept, I love the ceremony of it,” he said in 2022. “God ain’t done with me. We’re gonna figure it out.”
But even before his fatherhood journey began, Cannon had his fair share of high-profile relationships, including flings withKim KardashianandChristina Milian.
Here’s a look back at Nick Cannon’s dating history.
Christina Milian
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Cannon’s first public relationship was with singer and actress Christina Milian, whom he met on the set of their 2003 romantic comedy,Love Don’t Cost a Thing— a remake of 1987’sCan’t Buy Me Love. Cannon played the nerdy Alvin, who bribed popular girl Paris (Milian) into dating him for two weeks in exchange for free car repairs.
“I started dating Christina Milian from that movie,” Cannon toldInternational Business Timesin 2018. “We didn’t start dating until the very end of the movie, so it was actually cool because it allowed the chemistry to actually be real and really work.”
In 2005, he called her his “best friend,” adding, “I care for her and have great respect for her.” However, the couple broke up later that year. Though neither Cannon nor Milian commented on the split at the time, fans had long suspected that Cannon cheated on her after the release of her 2006 breakup anthem “Gonna Tell Everybody.” In 2019, Milian revealed onE! News' podcastJust The Sipshe had found incriminating text messages on his phone.
“I was reading for like a month,” she said. “I was reading messages.”
Shortly after Milian’s 2019 interview, theWild ‘n Outhost claimed he didn’t actually do anything wrong. “I wasn’t cheating. You got to be in a relationship to cheat,” Cannon explained during a radio appearance, perE! Online. “If I am careless enough to allow myself to get caught, then that means I wanted to get caught. The word is ‘careless.’ You know what careless means? ‘I could care less.’ I was at an age where I didn’t care.”
Kim Kardashian
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Cannon first metKim Kardashianwhile she wasworking as a stylistonMoesha. At the time, the futureKeeping Up with the Kardashiansstar was still datingRay J— but after their 2006 split, Cannon pursued her. The couple ultimately dated from late 2006 to 2007. “I was really into her, I was vibing,” he said in a 2021 appearance onDrink Champs. “She broke my heart.”
There aren’t any hard feelings between the two, though. “She’s a great girl!” Cannon said in 2014. “Her and her family are some of the most incredible people I’ve ever met in my life.”
Selita Ebanks
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Cannon and Victoria’s Secret modelSelita Ebankshad known each other for years before they ran into each other at a Super Bowl party in Miami in January 2007. But it wasn’t always a picture-perfect relationship; from there, Ebanks had to “clean up” Cannon’s act.
“Selita’s amazing,” he told PEOPLE at theVanity FairOscar party the next month. “She changed me — I’m no longer a player. She changed everything.”
Cannonproposed to the modelin May 2007 after the two attended the Met Gala. The actor took her to Times Square in a Rolls Royce and proposed with a 12-carat diamond ring in front of a jumbotron reading, “Selita will you marry me?”
But after Cannon told PEOPLE in August that he was going to “take it slow” with their engagement, the couplebroke up in Octoberof that year.
“Selita and Nick are taking a break to focus on their careers but still very much love each other and remain the best of friends,” Ebanks’ rep said at the time.
Cannon confirmed the latter in December 2007, telling PEOPLE that he was “still cool” with the model.
Mariah Carey
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Cannon first met future wife Mariah Careyat the 2005 Teen Choice Awards, where Cannon presented Carey with the award for choice music R&B artist. But before they even stepped on stage, the two had abrief behind-the-scenes encounterthat changed everything.
But the pair didn’t spark dating rumors until 2008, when Carey cast Cannon as the love interest in her “Bye Bye” music video. In April of that year, Carey’s rep denied the two were dating; however, that same month, the couple were spotted getting cozy in Las Vegas.
After dating for less than two months, Cannon and Carey got married in a surprise wedding in April 2008. The two held asunset ceremonyat Carey’s Bahamian estate.
“We really do feel we are soul mates,” Carey told PEOPLE at the time. “I never felt a love like this was in the cards for me.”
Carey later revealed that Cannon had proposed to her twice — once with a candy ring pop that had a 17-carat diamond engagement ring hidden inside and a second time on a romantic helicopter ride.
In December 2014,Cannon confirmedthat he and Carey had separated. Prior to confirming their split, he told PEOPLE that he was trying to “stay positive” and get through life “one day at a time.” Theirdivorce was finalizedin November 2016.
The couple continue to co-parent their twins, taking their children to the 2017Kids Choice Awardsand theKidspace Children’s Museumin 2018. Cannon has since called Carey his “fantasy love,” adding that he didn’t think he would get married again.
“I did my best in this space, and now I feel like there’s anew journeyin my life,” he said in 2022. “I’m not going to backtrack and put myself in that situation again because it doesn’t get better than that.”
Jessica White
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After his divorce, theMasked Singerhost was linked toSports Illustratedmodel Jessica White.
“Nick was one of my best friends,” White said in a 2016 interview. “Nick and I will always be close no matter what. He has a beautiful heart, it’s not even about his looks, he has a good heart.”
Though they reportedly split, the pair have remained close — White posed naked alongside Cannon for the cover of his 2022 mixtapeRaw N B: The Explicit Tape. Later that year, Cannon and White reportedlypartied togetherin New York City over Halloween weekend.
Cannonspoke about his relationship with Whiteon a May 2023 episode ofThe Jason Lee Podcast. TheDaily Cannonhost called his ex “beautiful” and “my muse,” even admitting that he’s “still in love” with her.
He also spoke about White’s 2020 miscarriage, suggesting that she didn’t want to talk about the loss publicly because “she felt like there was a narrative” of “negativity” in the media about the mothers of his children.
“I take full accountability. I want her to share her true and honest story at any time,” he said. “These women will tell their story when their time, when they’re ready to do it. I want that. I don’t want to ever speak for any of them because I know they can speak for themselves. Even in times of pain, even in times of darkness, I’m leaning on them.”
Brittany Bell
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Cannon and model Brittany Bell reportedly met in 2015. The on-again-off-again pair share three children together: sonGolden “Sagon” Cannon, born in February 2017;Powerful Queen Cannon, born in December 2020; andRise Messiah Cannon, born in September 2022.
The two spend plenty of time together while raising their children, includingmajor milestonesandphilanthropic work as a family.

De La Rosa has been candid about her and Cannon’s “open relationship.” Although she has referred to theMasked Singerhost as her “primary partner,” she’s also said, “I just know in my heart of hearts that this isn’t my forever person.”
On a 2022 podcast appearance, she said: “I think I see monogamy for myself down the line, and this won’t get me there. But I love where I’m at, at this very moment. It’s just not my forever.”
In June 2022, she said she has aclose relationshipwith one of the other women whom Cannon has children with. Although she did not specify who, she said the two frequently get coffee or dinner together.
“She’s a beautiful human being and I wish her nothing but the best in this forever journey we’re a part of,” De La Rosa said. “The rest of the women I don’t know and never met, but I wish them all the best as well.”
Cannon and the DJ frequently spend time parenting their three children together, including posing forChristmas card photosand taking them onspecial holiday outings.
Alyssa Scott
Alyssa Scott Instagram

Cannon likely met model Alyssa Scott when she appeared onWild ‘n Outin 2019. They have two children: sonZen S. Cannon, who died in December 2021 at just 5 months old, and daughterHalo Marie Cannon, born in December 2022.
In December 2021, the talk show host shared thatZen died from brain cancer, revealing that shortly after his birth, doctors discovered a fluid buildup inside his head and a malignant tumor that required brain surgery.Zen’s health worsenedaround Thanksgiving 2021 as the “tumor began to grow a lot faster.”
“We were faithful and hopeful for that time,” Cannon said onThe Nick Cannon Show. “We carried on, he was still just playing with his brothers and sisters, I embraced every moment.”
In June 2022, on what would have been Zen’s first birthday, Cannon and Scott announced that they hadstarted a foundation supporting"hope, grief care and pediatric healthcare for families and children in need" in his honor. “June 23rd will forever be a day of celebration,” Cannon wrote. “A beautiful lighting ceremony to honor the life of an Angel. Zen’s birth has now transformed into ‘Zen’s Light.’ "
The couple made sure to pay tribute to Zen when his little sister, Halo Marie, was born later that year.
“December 14, 2022. Our lives are forever changed ❤️,” Scott wrote on Instagram. “Zen is in every breath I take. I know his spirit was with us in the room that morning. I know he is watching down on us. He shows me signs every day. I will hold onto this memory forever.”
She added: “I will remember the sound of Nick’s voice saying ‘it’s a girl’ and the look of everything we’ve been through flash across his face. I will remember the sound of her crying out with her first breath and feeling her heartbeat against mine.”
Bre Tiesi
Bre Tiesi Instagram

Cannon first met model and real estate agent Bre Tiesi when she appeared onWild ‘n Outover 10 years ago. Since then, the two have shared an “on-and-off” relationship, according to Tiesi. The couple took a break while Tiesi was married to former Cleveland Browns quarterbackJohnny Manziel; the twomarriedin a private ceremony in March 2018, and theirdivorce was finalizedin November 2021.
Tiesi gave birth to her and Cannon’s first child,Legendary Love Cannon, on June 28, 2022, in an “all-natural” home birth. She’s been open about why she chose Cannon to be her son’s father, saying they share “a beautiful relationship [where] everything is so supportive and positive.”
“I justrespect and love who he isso much as a person,” she told E! Online’sDaily Popin March 2022. “I thought about, ‘Do I want my son to be this person? Look at your characteristics, look at your personality, look at how you treat people.’ "
Tiesi has also publicly praised Cannon — in December 2022, she wrote that Cannon “always shows up” for their son. “Always present, happy, consistent, loving parent and an even better person!” she added. “We love u!”
LaNisha Cole
LaNisha Cole Instagram

Cannon and photographer LaNisha Cole welcomed their first child, daughterOnyx Ice Cole Cannon, on Sept. 14, 2022. The two hadn’t spoken publicly about the pregnancy, so Onyx’s birth announcement surprised fans.
“As we all know, I am not easily triggered and have quite tough skin and have always been an open book but not everyone in my family has that same level of strength,” he wrote on Instagram. “So I pray and ask others to please project all criticism and cynicism towards ME and not the loving and precious Mothers of my children.”
He added: Cole “is one of the most guileless, peaceful and non-confrontational kind souls I’ve ever witnessed, and only deserves to revel in this moment of blissful joy of motherhood.”
Cole has since said thatco-parenting with Cannonis a “breeze” since the two see “eye to eye.”
source: people.com