Keyshia Cole's Dating History

After nearly 41 trips around the Sun, and an illustrious career in the R&B industry, Keyshia Cole has plenty of interesting stories to tell – particularly about her love life. Most recently, the Oakland-born vocalist found herself caught up in a confusing entanglement with Antonio Brown, although that didn’t seem to play out the way that she had envisioned.

The Way It Is hitmaker rose to fame as a teenager, and by the time the late 2000s rolled around, she had made a name for herself thanks to her talent, hard work, and tenacity. It wasn’t long before she began mingling with other high-profile artists and celebrities, even entering romantic relationships with some of them.

Needless to say, it’s been a bumpy ride for the songstress, but that hasn’t stopped her from putting back on her rose-coloured glasses and keeping an optimistic view when it comes to the future of her love life every time that she gets knocked down. 

Check out our recap of Keyshia Cole’s romantic history.

In 2005, rumours began flying that both Cole and “Foolish” singer Ashanti (who was dating Nelly at the time) were both romantically involved with – and feuding over – musician and producer Chink Santana.

That same year, Santana and the mother of two released their collaboration, “Situations.” Though a lot of details about their rumoured situation were never made public, nearly a decade later Cole and Ashanti worked together on “Woman To Woman,” a song that finds them seemingly confirming all the drama, which even reportedly led to Nelly and Ashanti’s separation.

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Back in the day, Jeezy and Keyshia Cole were being poised to become the industry’s King & Queen of Atlanta. In 2006, they released their joint track, “Dreamin” and although they were beginning to spend more time together, the South Carolina native wanted to keep things between them lowkey, which she didn’t love.

According to the “Soul Survivor” artist, Cole once proposed to him, although he shot it down. “Keyshia asked me to marry her, bought me a ring and everything. She not gonna tell you different. I was grown enough to tell her, ‘Look, baby, that isn’t what it is right now. I’m trying to get my shit together. I’m trying to get my money, take care of me and mine,” he told VIBE Magazine in 2008.

However, Cole had a different story. “After this guy proposed to me, I was like, dang, this is everything a woman lives for: to be married, with a ring, to be able to represent something,” she revealed to Essence Magazine. “But for me, it was the opposite. I was scared. I’m just not ready for that. I’m not done with my goals in life. I just couldn’t submit. But I loved him. That’s the crazy thing about it.”

After finding out about Jeezy’s engagement to his current partner Jeannie Mai, Keyshia said, “I’m super proud of Jeezy and Jeannie. She’s a sweetie. She’s always been sweet. But I’m super proud of the fact that he actually has taken that step to love openly because I know that the thing was, it was something he didn’t feel like he could do because of where he comes from. So to know that that’s happened and that he’s happy, it’s not about the colour or the complexion. You Black or you white, whatever you are, Asian, Chinese, whatever you are, love is love. I think that everybody deserves to be happy. I’m super happy for both of ’em actually.”

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After not being loved out loud the way she wanted to with Jeezy, the 40-year-old moved on with former professional basketball player Daniel Gibson, who not only gave her a wedding ring, but also her first son – Daniel Hiram Jr., born on March 2nd, 2010.

The two were married a little over a year after their child’s birth, on May 22nd, 2011, and just a few months later they renewed their vows. Unfortunately for the new family, it wasn’t long before the athlete and vocalist separated for good in September of 2013, with Cole going on to file for divorce in 2017, citing “irreconcilable differences.”

During a 2017 appearance on The Real talk show, the “Heaven Sent” singer gave an update on how she and her ex were managing. “We’re friends, we’re friends. We’re co-parenting pretty amazingly for our son and I’m really proud of us both, honestly. All three of us. We’re all trying to work it out, it’s tough, but we’re friends and we do it for him.”

Despite her positivity, it’s been reported that Gibson “dragged the divorce on for years,” regardless of Keyshia’s public pleas to finalize and that a judge had to send him four warnings and threaten a fine in order to get him to court.

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After leaving her husband, Keyshia Cole found herself in the midst of yet another high-profile relationship with Birdman, this one being arguably her most controversial.

As we’ve seen in the past, the creative has a tendency to wear her heart on her sleeve, and as Instagram was beginning to blow up, she didn’t hesitate to use it to express her affection for Bird, going all out by filming a video of her grinding on top of a piano as two men danced in the background, uploading it to her feed and tagging her beau’s handle.

While that moment was kind of chaotic, it had nothing on what would unfold when the R&B diva took a trip to the Cash Money Records CEO’s L.A. condo, where she crossed paths with another woman and accused her partner of cheating on her, leading Keyshia to attack her man’s guest.

The victim was allegedly scratched, had her hair yanked, and was punched in the face, which resulted in Cole’s arrest. She ultimately won $100,000 in her lawsuit against the singer; the incident is reportedly what lead Birdman to break up with the R&B star.

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One of Keyshia’s more brief flings was with Bow Wow, who first sparked rumours after he posted and deleted a photo in bed with a woman who looked like Keyshia in February of 2016.

Just a few weeks later, gossip about Cole egging Bow Wow’s car after their split surfaced online, however, the mother of two has consistently denied that it was her. Funnily enough, whoever the culprit was ended up hitting the wrong car, nailing Shad Moss’ friend’s vehicle instead of his own.

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While working to finalize her divorce from Daniel Gibson, the songstress and Floyd Mayweather made flirty headlines, although in an interview with Hot 97 she admitted that she’d “never survive in a relationship with someone like Mayweather.”

“You know I’d never survive in that equation. I might as well stay with my husband. That makes no sense,” she said at the time. “Even though I super love Floyd. That’s gonna be my friend to the end. I really do have a vibe with Floyd. I love him and he’s been very supportive. Just even giving me inspiration and words of encouragement.”

“Being in a relationship with Floyd, I would be totally hurt in shambles, I’m not that type of girl to be able to deal with that kind of stuff and I don’t think money would make that any better.”

Though she denied any involvement with Mayweather, at the same time she confirmed that she was talking to someone else in the entertainment industry, and “taking things really slow.”

The next time Keyshia Cole fell in love, it was with a much younger man – recording artist Niko Khale, who she went public with in early 2018. Despite their 14-year age gap, the two seemed to be in love and welcomed a son together, Tobias Khale, on August 1st, 2019.

Of course, their relationship wasn’t without its issues. In February of 2019 they sparked breakup rumours after fans noticed that the 40-year-old had removed all of her photos with him. In October of 2020 he confirmed that he and Cole had broken up, responding to a fan in his IG comments, “My heart is broken. My mind is open. My times approachin.’”

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And of course, Ms. Cole’s most recent fling with NFL star Antonio Brown has been all over the news cycle this month. The two first made headlines after teasing that the “Let It Go” singer got an “AB” tattoo ahead of the arrival of their “Don’t Leave” single, which certainly drummed up a lot of attention.

It was a while before we heard from them again – this time, we saw her tell her Instagram followers that she was missing her rumoured boo “a lot,” although he didn’t seem to take kindly to her public display of affection, later hopping on Live to publicly declare, “We don’t want you, Keyshia Cole.”

Brown’s antics don’t exactly come as a surprise to his fans, although many social media users have spoken out in defense of the industry legend after she was hit with such blatant disrespect.

While things may not have worked out with AB, Cole still has plenty of time to find the “Love” she’s been crooning about since 2005.