The Truth About Vanessa Williams' Complicated Love Life

Vanessa Williams has it all figured out when it comes to the world of showbiz. She shot to fame after winning the Miss America title in 1983 (the first Black woman to do so), has had an illustrious career as a recording artist, and became a force to be reckoned with in Hollywood. Although scandal cut short her reign, Williams continued to redeem herself in the public eye and let her work speak for itself.

But that sort of success did not translate to Williams' love life. The "Ugly Betty" star's relationship history has followed what some might call the Facebook definition of "complicated." After three marriages, four children, and two divorces, Vanessa Williams is now candid about the ups and downs of her current and former relationships, and does not shy away from sharing the lessons she learned along the way.

Tag along as we take you on a deep dive into Vanessa Williams' rather complicated relationship with love.

Before Vanessa Williams became a symbol of glitz and glamour, she was a self-described rebellious teenager who frequently found herself in trouble with her parents. When she was in high school, she started dating college freshman Bruce Hanson. She became pregnant and later decided to have an abortion — a secret well kept from her parents. "Being pregnant is the most frightening thing that happens in your life. I knew in high school that's something that I was not prepared to do, or fight, or struggle with," she told Nightline.

According to a 1985 Rolling Stone profile, Williams and Hanson had been together off and on for about three years. He followed her to Syracuse University. "We had this very intense relationship," she said. Williams' parents did not approve of their relationship. In addition, once nude photos were published of Williams in Penthouse, her relationship with Hanson grew rocky. As she dealt with the fallout, her lawyers and PR people advised her to not speak on the controversy. Hanson told her, "I'm your boyfriend. You can tell me everything." But Williams listened to her advisors and kept quiet. Soon after, she and Hanson broke things off.

Nowadays, it may be hard to imagine the huge deal the Penthouse scandal was, but this took place in the '80s, before smartphones and leaks of celebrity nudes. But the Miss America pageant prided itself on its squeaky clean image — it had a morals clause that Vanessa Williams reportedly broke. Shortly after breaking up with Bruce Hanson, a then-23-year-old Williams met 33-year-old Ramon Hervey II, who was hired as a publicist to resurrect her image. After the Penthouse scandal, she was forced to give up her Miss America crown in 1984. However, Hervey was privy to Williams' situation, and the pair bonded over not just work, but their backgrounds as well. 

Hervey soon defended Williams in the media, not just as a seasoned PR professional, but later as her boyfriend. Unlike Hanson, he didn't feel jealousy over the published images, since he hadn't been dating her at the time they were taken. "There's also a lot worse things she could have done. She could be a drug addict. She could abuse children. She could be a chronic drunk driver," he told Rolling Stone. 

Still, Williams' parents weren't too keen on this relationship, either. Her mother once urged her to reconsider jetting off to Australia with Hervey for a work trip, concerned for the image her daughter was presenting to the world.

Vanessa Williams' parents eventually came around. In a span of a few months, Ramon Hervey II introduced the idea of marriage to her mother. "I love your daughter, and I want to marry her eventually, and I don't want it to be a battle," Hervey said, according to Williams in a Rolling Stone feature. He added, "I know you want her to be independent and have her own place and decorate it. And I encourage her to do that, and I would never discourage it."

In 1987, Williams and Hervey tied the knot in Manhattan. Williams and Hervey had three children – Melanie Hervey, Jillian Hervey, and Devin Hervey — together, and continued to work together to advance Williams' career in showbiz. "My husband was my manager so we were working on my career together along with raising children," she told Glamour. However, the relationship started fizzling out. "The kids' schedules came first and my career came second, even though I was the main moneymaker. Unfortunately that meant the marriage came third."

Ten years after their wedding, Vanessa Williams and Ramon Hervey II filed for divorce in 1997. The marriage was marred by issues of infidelity, she noted in an interview with Glamour. "I hung in there for a while, until there came a time when I couldn't anymore." When news of their divorce broke, Williams told Jet Magazine that it was difficult to leave although she was "very miserable."

Williams felt pain, anguish, and most of all, embarrassment when she came to terms with her failing marriage. She recalled happier times portrayed in magazines. "And then being Catholic, and being on the cover of Ebony with the family, and having to say, 'He isn't all what he's expected to be. You know, I didn't make the right choice.' It's failure. Failure is humiliating."

Williams further emphasized that while she and her ex-husband worked as a team, the reason she left a mark in the entertainment industry was her talent. 

A year after Vanessa Williams' split from Ramon Hervey II, the actor met then-Los Angeles Lakers player Rick Fox. Sparks flew instantly. Williams was attracted to the athlete because "he was mature for his age, and he wanted me from the beginning,” she told The New York Times. But Williams approached the relationship cautiously.

She was also on the fence about their age difference — Fox is six years younger than she is. The singer's mother, Helen Williams, also did not approve of their relationship. "Rick is a very different personality. And he really pursued Vanessa. You have two celebrity mentalities and minds clashing at some point. So that did not surprise me," she told The Root.

However, Fox eventually swept Williams off her feet. "He said that if I don't marry you, I am not going to marry anybody else,” she recalled. ”That was very comforting." A few months later, the couple were engaged to be married.

In the summer of 1999, Vanessa Williams and Rick Fox eloped in the Caribbean, and later in September, the duo tied the knot once again in a church in New York. To avoid the mistakes from her first marriage, Williams wanted to do things differently — one of which was maintaining her financial independence.

The couple also kept his-and-hers homes (his on the West Coast, hers on the East Coast) for logistical purposes. In 2000, the couple welcomed their first child – Sasha Gabriella Fox — together. Fox especially loved to splurge on Williams and buy expensive presents for her. He installed a tennis court at their Chappaqua house — where Williams spent most of her time — a Patek Philippe watch to celebrate their first Christmas together, and a silver Mercedes on Mother's Day after the birth of their daughter.

The early marital bliss, however, was short-lived.

In 2004, just five years into their marriage, Rick Fox pulled a shocker and filed for divorce. The Lakers star publicly announced the decision via his spokesperson, Staci Wolfe, before discussing it with his then-wife, Vanessa Williams. Wolfe, in a statement, said, "They are both extremely devoted parents, so the most important thing to them right now is the welfare of their child. They are committed to working out what's best for her."

Williams was deeply hurt about the way she found out, although an insider told People that the divorce was not "entirely surprising, since they've spent their entire marriage living on opposite coasts." Amidst speculation that the couple was actually still together, Wolfe told the National Enquirer, "They are heading for a divorce and have been so for the last 18 months. They've virtually been leading separate lives."

At the time, the couple gave no official reason for the split.

Vanessa Williams faced a different set of problems during her second marriage. With Rick Fox, she worried about being too old for him. Moreover, scheduling conflicts put a strain on their relationship. "We had a different set of issues from those of my first marriage, mostly because we weren't on the same coast for most of it: He was on the road or out in Los Angeles, and after our daughter was born, I was on the East Coast, raising four children and flying across the country every two weeks," she told Glamour.

Given their professions, she recalled that "proximity was a tremendous obstacle," and she noted, "My expectations of a relationship had a really high benchmark because of my father. He was so good at everything ... My father was my example of what I expected to find in a partner. And that's impossible for anyone to live up to."

Despite the shock of the divorce filing for Williams, the two split amicably and remained good friends — so much so that Fox made an appearance on her show "Ugly Betty" in 2007.

After the end of her second marriage, Vanessa Williams focused on her career and raising her four children. Dating proved to be challenging due to the lack of free time — her packed schedule included filming for "Ugly Betty" and "Desperate Housewives," as well as performing on Broadway. She was also worried about how to approach this matter with her youngest daughter, who was off to college then.

It was in 2013 when Williams was introduced to now-husband and businessman Jim Skrip on a cruise in Egypt, via her interpreter. The actor recalled their meeting on "Live with Kelly and Ryan," telling the hosts, "My traveling companion, who is my interpreter, sat next to him ... [She said], 'He's traveling alone, why don't you talk to him?' ... We started talking sports and it was my last night, and I said, 'You want to have dinner at my hotel?' Outside ... We had a lovely three-hour dinner." 

It was then that Williams made the most of the opportunity and forced herself to open up and take a chance.

Vanessa Williams and Jim Skrip got married — twice! The couple first tied the knot on July, 4 2015, at St. Stanislaus Church. As a callback to the first time they met, the ceremony was Egyptian-themed. Skrip told People, "Honestly, when I saw Vanessa walking down the aisle, I didn't even notice her dress. We locked eyes and I got caught up in the moment, full of happiness and joy."

Williams and Skrip had another wedding a year later on Memorial Day in Upstate New York. Why two weddings? "We got married in Buffalo. His annulment was not done yet. So we had to get remarried in the Catholic Church," Williams said on "Live with Kelly and Ryan."

For her second ceremony, Williams walked down the aisle in a sleeveless Pamella Roland dress, which was light-colored and featured a soft pink sash. Williams wrote on Instagram, "Yesterday we took one last walk down the aisle – this time in my little church. Officially wedded Catholic. Amen! #MyJim." She also told People, "My friends just look at him and say 'God, he's solid. He's a real man. You want somebody in your life who has integrity, who is solid, who knows who he is, who is romantic."

Vanessa Williams' relationship with love has been a turbulent and complicated one. But she seems to have finally found her happily ever after with Jim Skrip. "Now that I'm on my third marriage, I've realized it's key to not expect one person to be able to fulfill every need in your life," Williams told Glamour. "I've got my friend who I go to the theater with, the friend I want to play tennis with. It puts a tremendous pressure on your mate to have to fulfill every desire you've ever had."

The star told Closer Weekly how she spends her free time. She does puzzles and loves it when friends and family come to visit. When asked how she and Skrip keep the flames burning, she responded with a laugh, "Being 56 and not raising children together."

From Miss America to singer and actor, Vanessa Williams has come a long way — including in love.