Stephen A. Smith has been the fiery voice of ESPN since 2003, known for his larger-than-life personality and quick wit. His trademark rants on-air made him one of sports media’s most viral figures, primarily through First Take, which he started hosting in 2012. Interestingly, however, Smith’s personal life remains shrouded in mystery, mainly out of the public eye.

We have seen long-standing rumors linking him to former co-host Molly Qerim, which he has publicly denied.  Even after admitting in past interviews that there is someone special, Stephen A. Smith continues to keep fans guessing about who truly holds his heart. Older pictures from 2023 recently resurfaced, showing him alongside a lady, whose name is unknown, chilling on a beach in Barbados, but it certainly wasn’t Qerim.

What happened with Molly Qerim and Stephen A. Smith?

Molly Qerim surprised everyone when she abruptly left the show she co-hosted with SAS on September 15, 2025. Molly had been with ESPN since 2006. She has been a part of First Take since 2015. Many believed her exit was related to Stephen A. Smith. But he revealed he was just as blindsided as everyone else.

According to Sports Business Journal reports, contract negotiations were the main reason behind Qerim’s decision. ESPN wanted her to stay and offered a $500,000 salary. But she considered it insufficient compared to her female colleagues, such as Malika Andrews and Mina Kimes. The discussions fell apart, and she chose to leave immediately, rather than prolong them any further. Qerim’s decision marked the end of an era on First Take.

On Instagram, she posted, “After much reflection, I’ve decided it’s time to close this incredible chapter and step away from First Take. Hosting this show has been one of the greatest honors of my career… I’m so grateful for what this journey has given me: lifelong friendships, unforgettable memories, and the chance to be part of something truly special. From the bottom of my heart, thank you for welcoming me into your homes.”

She admitted it leaked sooner than she intended. However, rumors about her alleged relationship with SAS persisted, which both have consistently denied at some point. Many have also linked the alleged affair to her divorce from NBA analyst Jalen Rose, whom she married in a private ceremony in July 2018.

Rose dismissed the Smith rumors as “laughable” and clarified that their split was based on personal differences. He expressed that he continues to have respect and love for both Qerim, stating, “We were friends before we were married, we just didn’t work as a couple.”

When and where was Stephen A. Smith spotted with the mystery woman? 

The first and only sighting of Stephen A. Smith with his rumored companion dates back to July 2023, when he was photographed enjoying a beach getaway in Barbados. Photos published by The New York Post showed the ESPN host relaxing and enjoying his Caribbean stay, in a resort alongside a brunette woman. The pair were seen lounging close together on sunbeds, sharing earphones, and at one point, she was spotted helping Smith apply sunscreen.

After Smith’s candid revelation on The Howard Stern Show in 2025 that “there is” a special someone in his life, fans scrambled back to the Barbados pictures. “But the industry has evolved to the point where, and I’m not bragging, I’m just speaking fact, I’m more popular than 95% of most of the athletes I cover. So as a result of that, you’re in the news constantly. So, you’ll know who that person is when she’s Mrs. Stephen A. Smith,” the ESPN analyst confidently said, still giving nothing away about his better half.

Stephen A. Smith’s relationship history

Stephen A. Smith, 57, has never been married, though he revealed in a 2019 GQ profile that he was once engaged,  an experience he admitted “didn’t work out.” But even then, as he was being pressed on why it didn’t, he quipped that it was none of their business, a line that he often delivers even on camera. There is little to no publicly known information about his two teenage daughters, despite the fact that the identity of their mother has also never been revealed.

In recent years, the most widely discussed speculation has linked Stephen A. Smith to his former co-host on First Take, Molly Qerim.

Smith’s brief comments on The Howard Stern Show only reignited public interest. His longtime friend Chris Russo shared a personal story, saying, “He has told me in the past, quietly, that, yes, he thinks there might be [marriage] down the road.”

“I want to get married someday. It will happen someday,” Smith then claimed. “He’s more romantic than you think he is,” Russo continued. He also added the vision that Smith wishes for, like proposing over a “candlelit, nice Italian dinner,” and “he won’t let anybody know about it!” So, does it mean that the ESPN analyst could one day surprise the public with a quiet, elegant proposal far from the cameras?

In true celebrity fashion, and despite the rumors, Smith has managed to maintain control over the narratives surrounding his personal life. His rumored relationships remain largely just speculation to this day.