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Wendy Williams has been experiencing some tough times lately, but there are rumors that she’s poised for a comeback. If so, the TV personality has probably learned a few things about recovering from painful events through her dramatic divorce from Kevin Hunter. If Williams ever walks down the aisle again, she will definitely do one thing differently. 

Why Wendy Williams skipped a prenup the first time around

Kevin Hunter and Wendy Williams ring the opening bell at the NASDAQ MarketSite in 2010
Then-married couple Kevin Hunter and Wendy Williams in 2010 | John Lamparski/WireImage

When Williams married her husband, Kevin Hunter, she assumed the relationship was going to last. According to Us Weekly, that led to an expensive mistake. 

The couple did stay together for over two decades, having a son together, Kevin Hunter Jr. But in 2019, Williams was blindsided by the fact that her husband was seeing another woman. Although this apparently wasn’t the first time he’d been unfaithful to her, this time he was expecting a baby with his girlfriend. 

Unfortunately, Williams’ early optimism about their marriage meant she never expected to need a contract. When a fan asked if the now-57-year-old would require a prenup if she got married again, she couldn’t help but laugh a little. “Abso-effing-lutely,” she said. 

Wendy Williams’ painful and expensive divorce

According to BuzzFeed, Williams isn’t the only star to make that mistake. Famous couples such as Johnny Depp and Amber Heard as well as Paul McCartney and Heather Mills also went into marriage without a prenup in place. One-half of each pair paid dearly for this choice when their marriage ended. 

For Williams, having a contract in place just didn’t make sense to her at the time. “I didn’t think it would end, first of all, and second of all, that is not sexy to introduce paperwork when you are in love with somebody,” the New Jersey native explained. 

To make the situation even more difficult, Hunter was her manager — another choice Williams regrets. “I don’t recommend that you work with your husband because I made him my manager and then when I decided to divorce him, he had to be fired,” she said. “In other words, I made him divorced and unemployed all in one day.”

Although it was an expensive lesson, Williams has clearly learned to protect herself going forward. And she appears to be interested in finding new love. 

Who has Wendy Williams dated since her divorce?

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Williams didn’t waste any time returning to the dating world. Distractify reports that just a few months after her split with Hunter, she started seeing someone new. While no one could fault her for wanting to enjoy herself, not everyone was sure her choice was a good one

The new guy, Marc Tomblin, was 27 years old and a convicted felon. That relationship didn’t last long. A month later she told fans she was dating a doctor in his 50s. 

In February 2021, she met a man named Mike Esterman during a segment of her talk show called “Date Wendy.” That seemed to ideal for Esterman, and the couple went out for a few months. Eventually, their busy schedules made it too complicated to continue seeing each other, and they called it quits. Three months later, she was spotted with a new man, but she didn’t share much information about him. 

Williams has struggled lately in her professional and financial life. Perhaps her love life is on the backburner while she figures out what’s next. But if Williams does ever decide to get married again, at least she’s clear on one thing: This time, she’s getting a prenup.