Tiffany Haddish is one of the most sought-after stand-up comedians in Hollywood at the moment, and it’s well deserved. Over the years, Haddish has proven her mettle, not only as a comedian but also as an actress, singer, and author. When it comes to her personal life, the Girls Trip star has always been an open book, sharing her traumatic past as a foster child to her struggle with motherhood and her romantic relationships, particularly her tumultuous marriage with her ex-husband, William Stewart, which ended in an ugly legal fallout.

Now, Haddish is once again making headlines for her parenthood rumours. The comedian’s recent Instagram post showing her cradling a baby alongside her long-time friend Jason Lee sent fans into a frenzy, sparking rumours that the 45-year-old star had quietly stepped into motherhood. Lee later clarified that the baby is his cousin’s 6-month-old grandson, Major.

The buzz around Tiffany’s motherhood status has once again ignited curiosity about her past relationships, particularly her former marriage to William Stewart and her later breakup with rapper Common. Here’s a closer look at Tiffany Haddish’s complex romantic history, why her first marriage ended in a legal battle, and why she’s now choosing to date multiple men while maintaining celibacy.

Who is Tiffany Haddish’s ex-husband, William Stewart?

Before she became a household name, Tiffany Haddish was a struggling comedian navigating pain, poverty, and a series of unstable relationships. In 2008, the comedian tied the knot with William Stewart, an Army veteran who later worked in entertainment, including as a Paramount executive. The two reportedly met on a plane in 2001, and their connection grew over time.

William has played a crucial role in Tiffany’s life, as he was the one who helped track down her estranged father before their marriage so he could walk her down the aisle. Haddish once described the moment as ‘one of the happiest days of my life.’ 

Tiffany and William’s marriage was marked by highs and painful lows

Despite being the one who gave her one of her best memories, the happiness in Tiffany Haddish and William Stewart’s marriage was short-lived. In her bestselling 2017 memoir, The Last Black Unicorn, the Black Mitzvah star alleged that Stewart was physically and emotionally abusive.

Haddish mentioned in her memoir that her marriage to Stewart became so toxic that she filed for a divorce in 2011. She also claimed that they had married and divorced twice, though her ex-husband refuted these claims. Their divorce was finalised in 2013, marking their legal separation. Tiffany later revealed that after their separation, she feared for her safety and accused Stewart of stalker-like behaviour.

Haddish’s claims didn’t sit well with Stewart, and he denied all allegations. He even went on to sue the comedian and her publisher for defamation, libel, and slander. In 2022, he released a tell-all book titled Trust, Lies, and Deceit: The Real Tiffany Haddish Revealed, offering his side of the story. Though the lawsuit’s status remains unclear, it’s evident that the marriage ended with deep emotional scars on both ends.

Tiffany’s high-profile romance with rapper Common

The years following Haddish’s divorce were a mix of breakthrough professional success and numerous personal breakdowns. From her breakout role in Girls Trip and winning an Emmy to confronting controversies, not to mention her multiple miscarriages, the comedian weathered storm after storm.

Then came a high-profile romance with popular rapper and actor Common. The two began dating in 2020, after the rapper allegedly pursued her for two years. In an interview with PEOPLE, the actress shared:

“The only celebrity I’ve entangled with, it was two years of him chasing me down before I finally was like, ‘Okay, let’s do something.’ That was top of 2020, but we met at the beginning of 2018, 2017.”

Tiffany Haddish and Common’s relationship initially appeared to be a fairytale. At one point, the comedian even described it as the “best relationship” she had ever been in. But fans were taken by surprise when the couple quietly split in August 2021. While Common later framed the breakup as a mutual decision, Haddish disagreed, revealing it was more his choice than hers. Reflecting on his past relationships, Tiffany told The Washington Post:

“It wasn’t mutual. It was more him saying, ‘I think this relationship has run its course’… It’s every two years… six to nine months single, then two years on. That’s his cycle.”

Why Tiffany is now dating multiple men (and staying celibate)

After a history of failed marriage, relationships, and even motherhood, standing today, Tiffany Haddish isn’t looking for ‘happily ever after, ’ at least, not in the conventional sense. In a recent PEOPLE interview, the Night School star revealed she is currently dating multiple people at once, but she has been celibate since October 2024. She said:

“I’ve been celibate and it’s working… It’s like men love you even more. They take you on trips. They be in love. And I’m like, ‘We in a relationship? I thought you were just taking me to eat.’”

Tiffany Haddish now has a new definition for commitment. While she still hopes to find a life partner and potentially even have a kid, marriage is no longer on her radar. What are your thoughts on her unconventional take on relationships?

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