If it’s one thing fans of The Real Housewives of Atlanta alum Cynthia Bailey know about the former supermodel is that she has a philosophy to love them and leave them when she’s no longer happy. Outside of her two marriages, she’s had some eye candy by her side over the years. Bailey is known to gush about her love life, including her romance with actor Leon Robinson, whom she shares her one and only child with. As it turns out, Bailey could have potentially been Mrs. Jackson. She recently revealed she dated a member of the famous musical family.
Cynthia Bailey reveals she dated Jackie Jackson
Bailey has dated some of the most iconic men in the industry. She’s been open about her past relationships with music mogul Russell Simmons, she was engaged to NBA player Jayson Williams, and even Soul Food alum Boris Kodjoe. But one person she never revealed until now is a member of the legendary Jackson family dynasty.
“I went on a random date with Jackie Jackson from The Jackson 5,” she told Jasmine Brand on her new FOX SOUL talk show, Brutally Honest. “Actually, I think I went on a couple of dates with him, and he was pretty cool,” she remembered. “He even picked me up from the airport. That’s like extra cool. Like, who wants to go pick up somebody from the airport? Especially LAX. It was crazy.
It’s unclear how long their romance lasted or what time period they dated. But Bailey didn’t have any hard feelings about their split. It’s also unclear if they’ve kept in touch since they stopped dating.
Jackie Jackson’s love life and career
Bailey isn’t the only beautiful woman Jackson shared his company with. The oldest Jackson brother has been married three times and has four children. After five years of dating, he married Enid Arden Spann. They divorced in 1986, with Spann getting a restraining order against Jackson, alleging he was physically abusive. They had two children together.
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In 2001, he married his second wife, Victoria Triggs. After their divorce, he wed his third wife, Emily Besselink, in 2012. They share twin sons.
Outside of his marriages, Jackson had an affair with Paula Abdul. He also dated Waiting to Exhale actress Lela Rochon for two years.
The ‘RHOA’ star has been married twice
While Bailey’s list of men in Hollywood she’s dated is impressive, she’s only said “I Do” twice. Before marrying Peter Thomas, Bailey was coined the “runaway bride,” having been engaged five times. Thomas and Bailey wed in 2010. But after years of financial trouble, cheating rumors, and bad business decisions on Thomas’ end that always went public, Bailey filed for divorce. Their divorce was finalized in 2017.
In 2020, she married sportscaster Mike Hill. She insisted that Hill would be her forever. But months before their two-year wedding anniversary, they split. Bailey confirmed the divorce days after their anniversary. The divorce has already been finalized. She says incompatibility and their friendship deteriorating led to the divorce.
