Jada Pinkett Smith, over the years, has become a mainstay in Hollywood — not only as a successful actor but also as a talk show host. Her bold choices in acting and her candid discussions about her battle with alopecia areata make her a trooper in more ways than one. But it’s not just her career that’s been in the spotlight, her romantic link-ups and boyfriends have also captured the public’s imagination.

Interestingly, some of the most talked-about episodes of Pinkett Smith’s famous talk show Red Table Talk revolve around Pinkett Smith’s romantic life, including her highly publicised marriage to superstar Will Smith and her “entanglement” with singer August Alsina.

In 2020, Pinkett Smith revealed that her involvement with Alsina occurred during a break from her marriage to Smith in 2015. In 2023, Jada disclosed that she and Will were separated for a considerable time, though they hadn’t filed for divorce and were keeping the relationship open.

From experimenting with an open relationship to dating a younger man, Jada Pinkett Smith has explored it all in the realm of dating and relationships. Her tell-all memoir, Worthy, which hit the shelves on 17 October 2023, delves into the intricacies of her whirlwind romance with Smith and their subsequent separation.

However, if you’re itching to delve into Jada Pinkett Smith’s dating history and past boyfriends, we’ve done the research for you and compiled a list of all the men that Pinkett Smith has been romantically involved with.

Jada Pinkett Smith’s dating history and boyfriends

 jada pinkett smith dating history
Picture Credits: Instagram/Jada Pinkett Smith

Let’s flip through the pages of Jada Pinkett Smith’s romantic escapades over the years, including Will Smith.

Grant Hill (1992 – 1995)

 jada pinkett smith dating history
Picture Credits: Instagram/Grant Hill

The first celebrity that Pinkett Smith dated back in the ’90s was American basketball player Grant Hill. Their paths crossed when she was a budding actor on A Different World and Hill was playing at Duke University. The details of their initial romance remain a mystery, but in 1993, Pinkett Smith shared with the LA Times that she was quite smitten by Grant’s innocence and grounded attitude.

Their romance may have been short-lived, but in a holiday-themed episode of Red Table Talk in 2018, Jada revealed that Hill was the first boyfriend she ever introduced to her family during the holidays. They even reunited at the 2017 NBA Awards and have remained friends over the years. Pinkett Smith went on to marry Will Smith in 1997, while Grant Hill married singer Tamia in 1999.

Wesley Snipes (1993)

Picture Credits: Instagram/Wesley Snipes

In 1993, while Jada was still seeing Grant Hill she had a brief fling with actor Wesley Snipes. Their dating rumours sparked after they attended the 21st Annual AFI Lifetime Achievement Awards. Not much is known about their relationship, and it fizzled out soon as nothing concrete was built from their red-carpet romance.

Tupac Shakur (1986 – 1988)


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The next iconic name in the list of Jada Pinkett Smith’s boyfriends is the late legendary rapper Tupac Shakur. Pinkett Smith appeared in several of the rapper’s music videos in the 1980s, including Keep Ya Head Up and Temptations. When Shakur faced accusations of sexual abuse in 1995, Pinkett Smith famously contributed USD 100,000 towards his bond. However, some reports clarified that they were close friends and collaborators rather than lovers. 

In the 2003 documentary, Tupac: Resurrection, Pinkett Smith opened up about her profound bond with the late rapper, describing it as more than friendship.

Will Smith (1995 to present)


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A post shared by Will Smith (@willsmith)

The next name to go down in Jada Pinkett Smith’s dating history is her long-time on-and-off partner Will Smith. The two began dating in 1995, but their connection had roots in the early 1990s when both were aspiring actors. Pinkett Smith was just 19 when she crossed paths with Smith during an audition for a role as his girlfriend on The Fresh Prince of Bel-Air. Although she lost the role to Nia Long due to her height, Pinkett Smith left a lasting impression on Smith, who was married to actor Sheree Zampino at that time. However, destiny had plans to bring Smith and Pinkett Smith together. 

Smith divorced Zampino in 1995 and wasted no time in pursuing a relationship with Pinkett Smith. In December 1997, they tied the knot in a private ceremony in Pinkett Smith’s hometown of Baltimore, MD. The couple now has two children together, Jaden Smith and Willow Smith, in addition to Smith’s son from his previous marriage, Trey Smith.

Their relationship, marked by intense speculation and rumours, has faced its share of challenges, including a period of separation and an exploration of an open relationship. In 2013, Pinkett Smith 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 later clarified that this didn’t mean they had an open relationship but rather a mature and trusting partnership.

In a surprising revelation during a recent sit-down interview with Today in October 2023, Pinkett Smith disclosed that she and Smith had quietly been living separate lives since 2016. Despite their separation, they haven’t pursued a divorce because of their commitment to working on their partnership. She confirmed on the show that they are in a healing space and working on their relationship again.

August Alsina (2017 – 2019)

 jada pinkett smith dating history
Picture Credits: Instagram/August Alsina

A controversial name on the list of Jada Pinkett Smith’s ex-boyfriends is the young singer-songwriter August Alsina. Their paths crossed through Jada’s son Jaden Smith in 2017 when Alsina was just 29 and Pinkett Smith was 49 years old. The word “entanglement” gained notoriety in 2020, thanks to this relationship. In June of that year, Alsina revealed to The Breakfast Club’s Angela Yee that he had been in a relationship with Pinkett Smith, with the blessings of Will Smith.

However, just 10 days after Alsina’s claims, Pinkett Smith addressed the situation in an episode of her talk show on 10 July 2020. During the episode, she revealed that, in 2016, she and Will decided to take a break, during which time she formed a friendship with Alsina that evolved into a romantic entanglement, as she famously put it.

Alsina responded with a song titled “Entanglements”. Though their connection was short-lived, the echoes of their supposed “entanglement” reverberated throughout the romantic corridors of Hollywood.

(Hero and feature image courtesy: Credits: Instagram/Jada Pinkett Smith and August Alsina)

Frequently Asked Questions (FAQs)

– How long did Jada Pinkett Smith and August Alsina date?
Jada Pinkett Smith and August Alsina dated for two years from 2017 to 2019.

written by.

Kratagya Rathore

Senior Digital Writer, Growth, Augustman
Kratagya Rathore could possibly be your passport into the world of style, grooming, skincare, and mindful living. Fashion is as imperative to him as his daily 10,000 steps count. He is a raconteur, almost living his life in a musical; A social firefly who is also fluent in silence. A journalism grad, Kratagya has previously worked for Times Internet and The Times of India.
Deconstructing Jada Pinkett Smith’s Dating History And Enigmatic ‘Entanglements’
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