During the Valentine’s Day taping of her Two Funny Mamas podcast with friend and co-host Sherri Shepherd, Whitley talked about the special place the singer still holds in her heart. The two met when they were young, growing up near each other in Shaker Heights, Ohio. They were were friends most of the time, but they blurred the lines and had a romantic relationship. She said a few of his songs were written with her in mind, including Levert’s “Addicted to You.”
“I called him one day…and I said, ‘I’m addicted to you.’ He said, ‘I’m addicted to you.’ And we started talking and I said that’s a song, Gerald! He made the song.”
But the two could never really make it work in the way that they wanted. He was an established singer with adoring fans and she was a burgeoning actress and comedienne trying to do her own thing. That didn’t work for him. She admitted that didn’t work for a number of relationships.
“Gerald needed a wife. He needed a real wife at home. He didn’t need an actress,” she said. “I didn’t understand that then and I remember he told me, it hurt my feelings. He said, ‘There can only be one star in this family.'”
“I didn’t understand that. I was like, ‘how dare you?’ But I get it now,” she added. “When you go on the road and you work like that and you come home, you don’t want your wife over there, ‘I gotta go to the Improv. I’m out!’ I did that to a lot of relationships.”
So they stayed close but saw other people. She was a support through all of his girlfriends and even a fiancée. He called her to complain about them, she joked. He ended up having three children by three different women and once spoke about regrets he had concerning how he handled himself in regards to the ladies he had his kids with.
“I wish I would’ve been smarter,” he previously said. “But at the same time, I’ve enjoyed my life so far and wouldn’t change it, especially my kids.”
He never married, and to this day, neither has she.
“We made a pact,” she said during the podcast. “We said when we turn 50 years old…if we’re not married at 50 we will marry each other.” Sadly, Levert passed away at the age of 40 in 2006. His shocking death was caused by an accidental overdose of a combination of prescription medication and over-the-counter drugs.
Looking back, he was the one who got away.
“I will always love Gerald,” she said. “Because it was a chapter in my life, I was so young. We went through so much as young people that I would say, I won’t say scarred me, but there were some things that happened with us that will make you as you grow up look back and say, ‘I guess I could have handled that differently.”
She apparently was the one who got away for him, too.
“There was an article in Sister 2 Sister magazine. If you really want to know how much Gerald cared about me, there was an article, he did an interview and I didn’t know. And he said, ‘The one true love of my life is Kym Whitley,'” she recalled. “It destroyed all kinda relationships. At the time I was engaged, [he] broke up with me from that one article.”
Despite that light blowup of her life, Whitley only has positive memories of the relationship, romantic and platonic, she had with Gerald Levert.
Looking at an image of him shown during the podcast, she remarked, “I wish he was still here. My life would be different. Even as just my friend.”