Since emerging into the spotlight in the 1990s, Jada Pinkett Smith has arguably become equally known for her acting career and her romantic relationships. Pinkett Smith launched her career with guest roles on shows like “True Colors” and “21 Jump Street,” but her role as Lena James in the sitcom “A Different World” propelled her into stardom. From there, Pinkett Smith starred in several popular flicks in the ’90s, including “Menace II Society,” “The Nutty Professor,” and “Scream 2.” Her career in the 2000s continued to soar with roles in “The Matrix” franchise and “Madagascar,” and by the 2010s, she starred in films like “Magic Mike XXL,” “Girls Trip,” and “Angel Has Fallen.”
Pinkett Smith is also recognized for her talk show, “Red Table Talk,” which she hosted with her mother, Adrienne Banfield-Norris, and daughter Willow Smith. Since its premiere in 2018, “RTT” has featured a number of notable guests, like Gwyneth Paltrow, Jordyn Woods, and Queen Latifah, and addressed topics like motherhood, relationships, drug and alcohol addiction, racial inequality, and more. The most popular of the “Red Table Talk” episodes, arguably, have revolved around Pinkett Smith’s romantic relationships, including her highly-publicized marriage to Will Smith and “entanglement” with singer August Alsina.
Outside of her marriage to Smith, the “Girls Trip” actor has garnered significant attention for her friendship with Tupac Shakur. Pinkett Smith met the late rapper at the Baltimore School for the Arts in the 1980s, and the two were close until his death in 1996. In a 2023 interview with RollingOut, she described her relationship with Skakur as a “soulmate friendship,” but despite the countless rumors, there was no romantic chemistry between them. “It was like God made us that way,” she explained. “It was like, look, I’m going to put y’all together, right? Y’all are going to be a dynamic duo. But I’m going to tell you right now, I’m going to make it so y’all are not going to be able to get together ’cause that just wasn’t the purpose.”
Ahead of the release of Pinkett Smith’s tell-all memoir, “Worthy,” hitting shelves on Oct. 17, here’s a breakdown of her dating history over the years, including the recent revelation that she and Smith quietly separated in 2016.
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Grant Hill
When Pinkett Smith was a young actor on “A Different World,” she met Grant Hill while he was playing at Duke University. While it is unknown when the two began dating, Pinkett Smith told the Los Angeles Times in 1993, “What I love about Grant is his innocence. He is grounded, not the spoiled type.” Though their relationship didn’t last long, “The Matrix” actor revealed in a holiday-themed episode of “Red Table Talk” that Hill was the first boyfriend she ever brought home for holidays. The two reunited at the 2017 NBA Awards, and appear to have remained friends years after calling it quits.
Getty / Kevin Mazur
Will Smith
Though Pinkett Smith began dating Will Smith in 1995, their connection was established years prior when the two were young actors in the early 1990s. At the time, Smith was making music with DJ Jazzy Jeff and starring in “The Fresh Prince of Bel-Air,” while Pinkett Smith was starting her career in “A Different World.” In a 2018 video interview with Vanity Fair, the “Magic Mike XXL” star revealed that she met Smith when she was 19 during an audition to play Smith’s girlfriend on “The Fresh Prince,” but ultimately lost the job to Nia Long for being too short. Smith noticed Pinkett Smith during the audition, but met Sherri Zampino that same day, and ended up marrying her in 1992.
Pinkett Smith made a lasting impression on Smith, and after his divorce from Zampino in 1995, he immediately wanted to give Pinkett Smith attention. The two began dating almost immediately, and in Dececember 1997, they tied the knot in a private ceremony in Pinkett Smith’s hometown of Baltimore, MD. In addition to Smith’s son from his marriage to Zampino, Trey Smith, the couple have two children together: Jaden Smith (born 1998) and Willow Smith (born 2000).
Over the course of their relationship, Pinkett Smith and Smith have been the subjects of intense rumors, with a prominent one being that the pair were in an open relationship. In 2013, the “RTT” host told HuffPost Live, “I’ve always told Will, ‘You can do whatever you want as long as you can look at yourself in the mirror and be okay.” She continued, “Because at the end of the day, Will is his own man. I’m here as his partner, but he is his own man. He has to decide who he wants to be and that’s not for me to do for him, or vice versa.” Pinkett Smith later clarified her comments in a Facebook post, writing, “Will and I BOTH can do WHATEVER we want, because we TRUST each other to do so. This does NOT mean we have an open relationship…this means we have a GROWN one.”
While they appeared on great terms in the public eye, the couple’s relationship was slowly deteriorating in private. In a sit-down interview with “Today” in October 2023, Pinkett Smith shockingly revealed that she and Smith had been quietly separated since 2016. “By the time we got to 2016, we were just exhausted with trying,” she said. “I think we were both kind of just still stuck in our fantasy of what we thought the other person should be.”
While the two have been living separate lives, she and the “King Richard” actor haven’t divorced because they are still trying to work on their partnership. “I made a promise that there will never be a reason for us to get a divorce. We will work through whatever. And I just haven’t been able to break that promise,” Pinkett Smith explained.
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August Alsina
“Entanglement” could have easily been Merriam-Webster’s word of the year for its viral use in 2020. In June of that year, singer August Alsina told “The Breakfast Club’s” Angela Yee that he had been in a relationship with Pinkett Smith, and actually had Smith’s blessing to do so. “I totally gave myself to that relationship for years of my life, and I truly and really, really deeply love and have a ton of love for her,” he explained. The news spread like wildfire, and Pinkett Smith was quick to shut down his statements.
However, just ten days after Alsina’s claims, Pinkett Smith addressed the situation in an episode of “Red Table Talk” on July 10, 2020. The sit-down included Smith, and during the episode, the “Menace II Society” star revealed that sometime in 2016, they mutually decided to take a break. Around that same time, Pinkett Smith formed a friendship with Alsina, and their relationship developed into a romantic one, which she famously referred to as an “entanglement” in the episode. Alsina responded to Pinkett Smith’s characterization of their relationship with his song, “Entanglements,” with lyrics that read in part, “Girl I know that we don’t call it a relationship / But you’re still f*ckin’ with me.”
