But have you always had such perfect taste in partners? What about your past? Unemployed exes? Uh, yeah.
Gabrielle Union is now flourishing as a working mom and wife of former NBA star Dwyane Wade. She often shares adorable videos of their blended family on social media, making them the ultimate relationship goals. However, her dating history hasn’t always been so rosy, marked by some questionable choices and red flags she seemed to overlook.
To understand Gabrielle’s rocky dating history, let’s go back to her junior year of high school. During this time, she caught the eye of a sophomore basketball player who is now known as Hall of Famer, NBA champion, and Dallas Mavericks head coach, Jason Kidd. In her memoir “We’re Going to Need More Wine,” Gabrielle reveals that many black guys weren’t interested in her due to colorism, so she felt a thrill whenever a lighter-skinned guy showed interest. When Jason noticed her at one of his games, Gabrielle was excited. Despite both having partners at the time, they exchanged numbers and, after a weekend of chatting, decided to break up with their significant others and start dating each other.
As her junior prom neared, Jason agreed to be her date. But two weeks before the event, after finishing a post-game interview, he dumped her right in the gymnasium, in front of his teammates and her dad. He had already moved on to someone else.
Jason went on to be drafted into the NBA, and Gabrielle adopted his dating strategy, always making sure she had a plan B, C, and D. In her memoir, she describes her 20s and 30s as a time of exploration. She enjoyed having multiple men in her life and thought that monogamy was overrated. She wanted to experience intimacy with different partners.
After a friend pointed out her preference for lighter-skinned men, Gabrielle began dating men of all complexions. In 1999, she started dating Jacksonville Jaguars running back Chris Howard. After six months, Chris decided to propose. Gabrielle flew to Jacksonville to celebrate her 27th birthday with him. She spent the day at the spa, and when she returned to his home, she found a trail of rose petals leading to Chris, who was on one knee with a potato wedge in one hand, a ring in the other, and a bucket of KFC next to him.
Looking back, she sees all the red flags, but at the time, she happily accepted his proposal. She called her friends, family, agents, and reps to share the news. The next day, she flew to Wilmington, North Carolina, for a “Dawson’s Creek” audition and returned to Jacksonville the same day. Checking her email on Chris’s computer, she found messages revealing that Chris had planned to fly in another woman if she had turned down his proposal.
Just 24 hours after getting engaged, Gabrielle faced a tough decision. Ultimately, she stayed with Chris, fearing public humiliation and backlash from her friends, family, and the media. Chris was cut from the Jaguars in 2000, and although her friends urged her to leave him, Gabrielle didn’t want to kick him while he was down. By the time they married on May 5, 2001—a wedding she paid for herself—Chris was training with the Raiders, but they eventually cut him too.
Gabrielle revealed that from that point on, Chris never found another job, leaving her to be the primary breadwinner. She supported all of his failed business ventures, all while he continually cheated on her. Surprisingly, Gabrielle wasn’t too upset about him seeing other women; since he was unfaithful, she felt she had the right to see other people too. But things came to a head in 2005 when Gabrielle landed the role of Alice Kramden in the film “The Honeymooners.” One of Chris’s mistresses decided to cash in on Gabrielle’s success. She contacted several media outlets to sell her story and prove that Chris was a serial cheater. Luckily, Gabrielle had strong industry connections, and an insider at a news outlet warned her about the woman’s intentions.
Gabrielle immediately hired Hollywood lawyer Marty Singer, known for solving such problems. According to Gabrielle, they set up a sting operation to meet with the woman and find out what she knew about Chris. However, the woman never showed up and disappeared. In her memoir, Gabrielle mentioned that she wasn’t even upset about the cheating; she was more upset about having to pay a lot of lawyers’ fees to fix Chris’s mess. The couple announced their separation in November 2005. In a statement, her publicist said they remained close and asked for privacy during this difficult time. Shortly after, her publicist’s phone was flooded with calls from eligible bachelors in the industry who were interested in Gabrielle. Their divorce was finalized in 2006, and since they didn’t have a prenup and Chris was financially dependent on Gabrielle, she had to give him a hefty sum to end their marriage.
Gabrielle moved on and reportedly had some sort of interaction with basketball player Vince Carter. At the time, Vince was playing for the New Jersey Nets, and one of his teammates was Jason Kidd. But that’s not even the most dramatic part of the story. We couldn’t find any photos of Gabrielle and Vince together, but their alleged fling took place around 2006. Now, we don’t want to gossip, but in 2006, Vince was still legally married to his wife of two years, Ellen Rucker. Actor and comedian Faizon Love spilled all the details during an interview on Kwame Brown’s “Bust Life.” Faizon described how, during a night out at a club, he ran into Gabrielle and Vince, and they were all drinking and having a good time. According to Faizon, he and Gabrielle shared a hot and steamy makeout session. He even said that anyone who didn’t believe him could just ask Vince for confirmation. Faizon added, “Ask him about that night. Everybody knows about the infamous Faizon Gabby tongue down.”
It seems like someone has gone to great lengths to erase any traces of Vince and Gabby’s rumored fling from the internet. This makes it tough for us to confirm, but here’s what we’ve found. RRG discovered a message board post from January 2007 on a basketball forum. In it, an anonymous user linked to a Metro News report suggesting that Gabrielle might have been the reason Vince got divorced in the summer of 2006. Regardless of whether that was true, whatever was happening between Vince and Gabby didn’t last long, and she soon moved on with Darren Sharper of the Minnesota Vikings. Back then, Darren was considered a hot catch and a definite upgrade from Gabrielle’s ex-husband, though looks can be deceiving.
During the summer of 2006, Gabrielle and Darren attended several red carpet events together, looking like the perfect couple. There aren’t any interviews with Gabrielle discussing their relationship, but it’s believed they were on-again, off-again. In January 2007, Gabrielle was seen “flirting and dirty dancing” with Derek Jeter at a Bahamas nightclub, though her rep insisted they were just friends.
A few weeks later, she met Dwyane Wade at a Super Bowl party. Gabrielle mentioned in an interview that she wasn’t interested in Dwyane because she was truly, madly, deeply in love with someone else. We’re not sure if that someone was Darren or another guy. Darren went on to date several other women in the industry, and ten years after his relationship with Gabrielle ended, he was sentenced to 18 years in prison for drugging and assaulting around 16 women in California, Nevada, Louisiana, and Arizona.
Back to Gabrielle and Dwyane. When they first met, Gabrielle wasn’t interested in dating another athlete, especially one as young as Dwyane, who was 25 while she was 34. Dwyane was also married to his high school sweetheart, Siovaughn, and they had two children together. So, Gabrielle and Dwyane decided to just be friends. Then, after what she described as a heart-crushing breakup with yet another immature jerk, she decided to give Dwyane a chance. And this is where things get a little complicated.
Dwyane Wade’s Tumultuous Love Life: Divorce, Scandal, and Redemption
In 2007, Dwyane Wade filed for divorce from his then-wife, Siovaughn, the same year he met Gabrielle Union. However, Wade insists that Gabrielle wasn’t the reason for his marriage’s downfall. The couple made their public debut in 2010, coinciding with the finalization of Wade’s divorce, and faced relentless media scrutiny, lawsuits, and even an unconfirmed allegation that Wade gave his ex-wife an STD. In May 2010, Siovaughn filed a case claiming Wade’s relationship with Gabrielle caused her and their children emotional distress, but the lawsuit was eventually dismissed. Wade was awarded sole custody of his two children in early 2011 and adopted his nephew, Davion Morris, that same year.
Wade recounted a contentious moment, stating, “I’m having somebody pick up the children during your parenting time for eight or nine hours because I want them to play basketball. What if it’s something I have planned and I want to take them somewhere? Please, I’m entitled to this.” The parenting coordinator, Howard Rosenberg, warned, “Ms. Wade, if you do not allow Zaire to go to that basketball game, I’m gonna go ask the judge that you never see your children again, and I’ll send you the email.”
Despite eventually reaching a divorce settlement in which Wade was ordered to pay Siovaughn five million dollars, the drama was far from over. In November 2011, an anonymous woman told the Bossip website that Wade “cheats on Gabrielle all the time,” adding, “I too had my situation with Dwyane. Can’t lie, he is great in bed, but I definitely would not take him seriously the way Gabrielle does.”
Two years later, in 2013, Wade fathered a child with his longtime friend Aja Metoyer, who also has two older children with actor Damon Wayans Jr. Wade and Gabrielle claimed they were broken up when the child was conceived, but TMZ uncovered Gabrielle’s social media posts from that period, suggesting they were still together. In her memoir, Gabrielle admitted they weren’t in a good place when Wade fathered a child with someone else. Her fertility struggles made the news even more painful, but she and Wade worked on their relationship behind the scenes, despite her struggle to forgive him. She wrote about the internal conflict, revealing that fear of public humiliation prevented her from leaving.
Aja gave birth to their son Xavier in November 2013, and less than a month later, Wade proposed to Gabrielle with an eight-and-a-half-carat diamond engagement ring. His children assisted by holding signs that read “Will you marry us?” Gabrielle said yes, marking a new chapter in their tumultuous love story.
“The biggest difference between this marriage and my last one is the prenup, which I insisted on. When you have your own assets, you don’t need to worry about anyone else’s, so it’s important to enter a relationship knowing we’re here for each other. Besides, I’ve never seen Dwyane balance a checkbook, which I find hilarious. I have to protect my own stuff.”
They signed the prenup and got married in April 2014. After experiencing nine miscarriages, they decided to have a child via surrogacy, and their daughter Kaavia was born in November 2018. These days, Gabrielle and Dwyane seem happier than ever. Dwyane also shares a bond with his son Xavier, although he chooses to keep their relationship off social media. Aja, who co-parents with Dwyane, landed a spot on the reality show “Basketball Wives” and told Bossip that they have a great co-parenting relationship for their son’s sake. However, she declined to comment on her relationship with Gabrielle.
Looking back on her decision to give Dwyane a second chance, Gabrielle is still torn. In her second memoir, she wrote, “The me of today wouldn’t have stayed with him, but would I be who I am now without that pain?””