Jada Pinkett-Smith and Will Smith may have tied the knot in 1997, but they each have their own romantic past. Their over two-decade marriage was even put on pause at one point, which paved the way for an “entanglement” between Jada and one of her friends (more on that below). HollywoodLife has broken down the iconic Hollywood couple’s most famous romances below!
As for Jada and Will’s own love story, it’s quite famous: Jada auditioned for the role of his character’s girlfriend on The Fresh Prince of Bel-Air in 1994, but at five-feet tall, the A Different World star was deemed too short (Will stands at six feet and two inches tall). The role ended up going to Nia Long, but after Will’s first marriage ended in 1995, he began dating Jada that very same year. After marrying in 1997, they welcomed two children — son Jaden Smith in 1998, and daughter Willow Smith in 2000 — and the rest is history! Now, let’s look back at their exes:
Jada Pinkett Smith
Jada dated the NBA star, who has played for teams like the Detroit Pistons and Phoenix Suns, between 1993-1995. On her Facebook Watch series Red Table Talk in Dec. 2018, the actress even revealed that the professional basketball player was the first boyfriend whom she ever brought home during the holiday season! After the relationship ended, Grant married singer-songwriter Tamia Hill in 1999, and the couple now share daughters Myla Grace and Lael Rose.
Jada’s infamous “entanglement” with singer August Alsina actually happened while she was on a break with Will. Jada met the 1992-born singer at her children Jaden and Willow’s set at the 2015 Wireless Festival in London, and the two sparked romance rumors (and therefore, divorce rumors between Jada and Will) in the forthcoming years. It wasn’t until June of 2020, however, when August claimed that Will allegedly gave the singer his “blessing” to date Jada, suggesting that they had an open marriage (something that Jada previously denied in a 2013 Facebook post).
“I totally gave myself to that relationship for years of my life, and I truly and really, really, deeply loved and have a ton of love for her,” August said of his relationship with Jada during an interview with The Breakfast Club’s Angela Lee in June of 2020. He added, “I devoted myself to it. I gave my full self to it. So much so that I can die right now, and be ok with knowing that I fully gave myself to somebody…. And some people never get that in this lifetime.”
After dropping that bombshell, Jada went on the record on her own talk show, Red Table Talk, to clarify that she had an “entanglement” with August while her relationship with Will was “over” at the time. Jada also explained that her relationship with August began as “a friendship,” because it “started with needing some help, and me wanting to help with his health and his mental state” (August has been open with his past opioid addiction).
In regards to August saying Will gave Jada his “permission” to let this new romance blossom, The Matrix Reloaded star said on her Facebook Watch talk show in July of 2020, “The only person who can give permission in that particular circumstance is myself. But what August was probably trying to communicate — because I could actually see how he would perceive it as permission, because we were separated, amicably — I think he also wanted to make it clear that he’s not a homewrecker, which he’s not.”
Actress Garcelle Beauvais made headlines when she revealed that she once dated Will during a May 2020 episode of The Real Housewives of Beverly Hills. She made this confession right in front of Sheree Zampino, who is Will’s ex-wife! “He was hot. He was a Bachelor, I was single, you know, it happens in Hollywood,” Garcelle confessed on the episode! However, Garcelle clarified that the relationship happened before Sheree’s marriage with Will (they tied the knot in 1992). Garcelle played Will’s love interest in the 1999 flick Wild Wild West — you can watch their infamous scene from the movie above!
Actress Sheree Zampino is Will’s most well-known ex, and his first wife. They married in 1992, and welcomed a son, Trey Smith, later that year. But after Will met Jada while she auditioned to be his character’s girlfriend on The Fresh Prince of Bel-Air in 1994, Will soon realized afterwards that he was meant to be married to Jada.
One night during a dinner with Sheree, Will said he had “a realization that [he] wasn’t with the person I was supposed to be with” and began “crying uncontrollably” inside the restaurant’s bathroom stall, which he recalled in an Oct. 2018 episode of Red Table Talk. However, Will knew he was “never getting divorced” and did not purse a relationship with Jada during the marriage — it was also Sheree who filed for divorce on Valentine’s Day in 1995.
“Divorce was the worst thing in my adult life. Divorce was the ultimate failure for me. I’ve been hurt a lot in my adult life, but I don’t think anything touches the failure of getting divorced from my 2-year-old son’s mother,” Will confessed to his wife, Jada, in a June 2020 episode of Red Table Talk.
To this day, Sheree and Will have maintained an amicable co-parenting relationship. “Will and I, when we got divorced, we have never had a relationship that doesn’t have Trey at the center of it,” Sheree said during a May 2020 episode of RHOBH (the same episode in which Garcelle revealed her fling with Will).