Home » Latest » Celebrity » Inside Wendy Williams’ Relationship History

Inside Wendy Williams’ Relationship History

6

InfoSearched 22 0 Celebrity

8.6

SaveSavedRemoved 2

Wendy Williams built a career on gossip, but her own love life gave the tabloids just as much material.

Long before she was dishing out “Hot Topics” segments from behind her desk, Wendy Williams was living out her own tabloid-ready romantic saga — one that stretches from a 1980s fling with an R&B singer to a televised dating contest in 2021. Nicki Swift’s video breakdown traces the talk show host’s relationships decade by decade, and the through-line is a woman who’s never been shy about narrating her own drama the same way she narrates everyone else’s. Two marriages, a string of hip-hop-adjacent dating rumors, and one very public reality-show-style courtship later, Williams’ relationship history reads like one of her own show segments.

• Williams’ first marriage, to Bert Girigorie in 1994, collapsed within five months amid claims of erratic behavior, drug use, and explosive arguments.
• Her marriage to Kevin Hunter Sr., which began in late 1997 and produced son Kevin Hunter Jr. in August 2000, ended in a 2019 divorce filing after Hunter fathered a child with mistress Sharina Hudson.
• Williams tried her hand at dating again in early 2021 with the “Date Wendy” contest, picking contractor Mike Esterman before the relationship fizzled by May 2021.

The Early Years and the Hip-Hop Circuit

Williams’ relationship résumé allegedly kicks off in the 1980s with a connection to R&B singer Sherrick, but it’s the 1990s where her dating life starts sounding like a who’s-who of hip-hop. She reportedly dated Eric B., one half of the legendary duo Eric B. & Rakim, and even went on a casual date with The Notorious B.I.G. around 1994 — an encounter Williams herself has described bluntly, noting Biggie was “definitely not my type.” It’s the kind of detail that only Wendy Williams could deliver with a straight face on her own show years later.

A Five-Month Marriage and a Chance Meeting at a Roller Rink

Before Kevin Hunter ever entered the picture, Williams was briefly married to Bert Girigorie in 1994. That marriage didn’t survive long — it fell apart within five months, with Williams later citing erratic behavior, drug use, and explosive fights as the reasons it couldn’t hold together. Later that same year, in what became one of the more famous meet-cutes in talk-show lore, she met Kevin Hunter Sr. at a roller-skating rink.

The Hunter Years and the Split That Made Headlines

Williams and Hunter married in late 1997, welcomed son Kevin Hunter Jr. in August 2000, and built a genuine media empire together — Hunter didn’t just stay her husband, he became her manager and the executive producer of “The Wendy Williams Show.” But behind the professional partnership, Williams has said the marriage was riddled with chronic infidelity. In her 2021 Lifetime documentary “Wendy Williams: What a Mess!,” she recounted that Hunter cheated on her even while she was on bed rest during her pregnancy.

She filed for divorce in April 2019 citing irreconcilable differences — just weeks after it emerged Hunter had fathered a child with mistress Sharina Hudson in March 2019.

The divorce officially finalized in January 2020, closing the book on a two-decade personal and professional partnership. It’s a split that echoes the kind of messy, business-entangled breakups covered in The Real Reason Phaedra Parks Got Divorced, where a marriage and a career were nearly impossible to untangle from each other.

Getting Back Out There: The ‘Date Wendy’ Contest

Adapting to single life in her late 50s wasn’t something Williams hid from her audience — instead, she turned it into content. In early 2021, she launched the “Date Wendy” contest right on her talk show, inviting men to submit applications for a shot at taking her out. She landed on contractor Mike Esterman, but the fling didn’t have much staying power; by May 2021, busy schedules had put an end to it. It’s a very Wendy Williams way to date — publicly, on her own terms, and packaged as a segment for the audience that’s followed every twist of her love life for years, not unlike how fans have tracked Inside Megan Fox’s Relationship History across tabloids and talk shows alike.

What Williams’ dating history really shows is that she’s never treated her personal life as off-limits material — she’s the one who put “Date Wendy” on the air in the first place. Whoever ends up in Wendy’s next chapter should probably expect it to be Hot Topics fodder before it’s anything else.