As Rumors Fly That She's Single Again, A Look At Brandy's Dating History

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In May it came out that Brandy was dating hip-hop artist Sir the Baptist, and while there was initially speculation about it, they got more and more comfortable putting their PDA on display on social media:

https://www.instagram.com/p/BUKu6QxltAR/?taken-by=sirthebaptist&hl=en

But just as fast as it got going, people are now wondering if it’s already over. Why? Because Brandy posted this message on Instagram:

https://www.instagram.com/p/BV3vOrkFoCy/?taken-by=4everbrandy&hl=en

It should also be mentioned that Brandy deleted all of the pictures and videos she had on her profile that promoted his music or that just featured the two together. There is no sign of him now. As for Sir the Baptist, images of Brandy and their relationship still remain on his page.

It’s no secret that Brandy, like many of us, hasn’t had the best luck at love. At one point, despite formerly being engaged, the 38-year-old singer said she didn’t see herself getting married. But before that comment, she sought advice for making relationships work because she said she did indeed want to tie the knot and find her forever love.

“I have had my heart broken to pieces,” she told The Daily Helpline in 2015. “But I just want to know the secret of making it work, cause time is ticking. I’m 35, and I’m trying to one day get to the next level. The next level! You know? Like marriage one day? Help me.”

With that being said, check out the singer’s history with love over the years. We’re still rooting for her to find her Mr. Right. It just wasn’t any of these guys.

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Kobe Bryant

While most of us just saw the burgeoning hoop star and singer go to to his prom together, in 1996, she had a brief relationship with him. In the image above, they were captured at the premiere for the film Eraser hand in hand.

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Usher

Brandy reportedly dated Usher briefly, who was also super popular at the time, back in 1998. He previously appeared on her old UPN show Moesha as love interest and classmate Jeremy Davis in Season 3 and 4.

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Mase

While she was putting together her album Never Say Never, Brandy briefly dated Bad Boy rapper Mase. He appeared on her hit song, “Top of the World.”

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Robert Smith

In 2001, Brandy started dating producer Robert “Big Bert Smith.” They kept their relationship out of the spotlight until 2002, when the singer became pregnant. They welcomed daughter Sy’rai, and on their reality show, Brandy: Special Delivery shared the pregnancy and their relationship, which they were framing as a marriage. A year after Sy’rai was born, they called it quits, and years later, Smith would reveal that they were never legally married. They told that tale in the hopes of keeping her public image pristine.

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Quentin Richardson

Another serious relationship, Brandy was engaged to the former NBA star, and their engagement lasted 15 months. She even got a tattoo of his face on her back, but when things ended, she had the ink changed.

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Flo Rida

In 2010, Brandy dated rapper Flo Rida, and even talked about their relationship on her VH1 reality show, Brandy and Ray J: A Family Business. She broke up with him, but he quickly, and briefly, moved on with model Eva Marcille.

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Terrence Jenkins

The actor and former co-host of 106 & Park dated Brandy after her relationship ended with Flo Rida. They were seen court side together at an NBA game and hit up an event or two as a pair. He, like Flo Rida, would move on to a model — Selita Ebanks.

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Ryan Press

Another serious relationship, Brandy and music exec Ryan Press were engaged in 2012. By 2014, they called it quits, to many people’s surprise. As she told us in 2015 about that split, “This last heartbreak was really hard, you know what I mean? It’s time. I just made a decision that even through heartbreak, you have to affirm that all will be well and in time you will feel better. And I feel better. I feel great! I feel strong. And I love it. I want everyone to feel strong because that’s when you can do it all–when you feel like you can.”