1. Brooke Shields and Michael Jackson
Every girl wanted to be actress Brooke Shields when she dated pop icon Michael Jackson back in the ’80s. Michael was Hollywood’s most eligible bachelor. And Brook was a supermodel. They are pictured together on a date in 1984.
Brooke and Michael are pictured with his brothers: (L-R) Randy, Jackie, Tito and Marlon. Michael loved to take Brooke out on the town and show her off. They loved each other’s company.
2. Jennifer Lopez and Wesley Snipes
Actors Jennifer Lopez and Wesley Snipes once dated briefly. They met on the set of Money Train in 1995. He asked her out repeatedly and she finally gave in. But there was no chemistry between them and she let him down easy.
Jennifer later said in an interview with Remezcla, “Wesley, even though I had a boyfriend at the time, went full court press. He was flirting with me — you always flirt with your co-leads — but he started getting a little bit more serious about it.”
She continued, “He would invite all of us out, and at the end of the night, he would sometimes try to kiss me. I would tell him, ‘Wesley, please, I don’t see you that way.'”
According to gossipmongers, they broke up because he was allegedly abusive toward her.
3. Prince and Kim Basinger
Pop singer Prince and actress Kim Basinger dated secretly in the ’80s. They are pictured dining at a Los Angeles restaurant in 1988. In another photo from this set, they hid their faces when the paparazzi spotted them. Kim, now 70, was best known as a Bond girl in 1983. She was ranked third on the LA Times Magazine‘s “50 Most Beautiful Women In Film.”
4. Tyra Banks and Seal
Model Tyra Banks and singer Seal dated in 1996. They are pictured attending the World Music Awards on May 7, 1996 in Monaco.
5. Nicole Kidman and Lenny Kravitz
Rocker Lenny Kravitz and actress Nicole Kidman were once engaged to be married.
According to People.com, Nicole rented an apartment from Lenny, and they eventually began dating. But Nicole was impatient, so she popped the question to Lenny.
“I get engaged and I get married — that’s my thing,” she told People.com. “I don’t want to date. I’m interested in a very, very deep connection.”
According to an interview with Vanity Fair, the romance fizzled and they broke off their engagement. “It just wasn’t right. I wasn’t ready. We weren’t ready,” she explained.
6. Whoopi Goldberg and Ted Danson
Everyone was shocked when actor Ted Danson dated actress/comedienne Whoopi Goldberg in the 1980s. They met while he was a guest on The Arsenio Hall Show in 1988. He described her as “a sexy, funny woman”. She described him as tall, dark and handsome. They fell in love while filming Made in America in April 1992.
Ted and Whoopi broke up after he appeared in blackface at a Friars Club comedy roast in honor of Whoopi. He told many racist jokes, and he received fierce backlash after his blackface photos were published in the tabloids. Whoopi initially defended him, saying she wrote the racist jokes, and she even helped paint his face.
7. Jay Z and Aaliyah
Some of you are too young to remember when Jay Z dated singer/actress Aaliyah Haughton. Aaliyah was also dating Damon Dash at the same time. Jay Z and Aaliyah are pictured with Bijou Phillips and Kidada Jones at a bar in Los Angeles, California. Aaliyah died in a plane crash in the Bahamas in 2001 at age 22.
Jay Z also dated rapper Foxy Brown, actresses Nia Long and Rosario Dawson; singers Mya, Blu Cantrell, Christina Milian and Rita Ora; and model Shenelle Scott (they are rumored to have a son together).
Jay Z finally met the woman of his dreams after he was arrested by the NYPD on April 13, 2001. The rapper and 2 other men were hit with a weapon charge after an unregistered handgun was found in their car. He accepted a plea deal and his criminal record was expunged. That same year, Jay Z met aspiring singer Beyonce Knowles and they began dating. The rest is history.
8. LL Cool J and Kidada Jones
L.L. Cool J dated Kidada Jones while he was with his long-suffering baby mama Simone Johnson. Kidada is the daughter of Quincy Jones. They are pictured attending the American Film Institute awards ceremony on March 4, 1994 in Beverly Hills, California.
LL and Kidada dated on the West Coast, while his common-law wife raised 2 of their four children (Najee and Italia) on the East Coast. Kidada eventually dumped LL and he went back to Simone. He married Simone in 1995 and they had 2 more children (Samaria and Nina).
9. Halle Berry and Christopher Williams
Halle Berry dated R&B singer/actor Christopher Williams while filming The Last Boy Scout in 1991. She famously accused one of her ex-boyfriends of abusing her. Many fans believed Christopher was her abuser. The rumors affected his career.
A frustrated Christopher accused actor Wesley Snipes of busting Halle’s eardrum during a severe beating. “I’m so tired of people thinking I’m the guy [who did it],” he said. “Wesley Snipes busted her eardrum, not me.”
10. Tom Cruise and Sofia Vergara
Tom Cruise and Sofia Vergara dated briefly in 2005. According to a report, Sofia received a mysterious call from Tom, inviting her to his upcoming birthday party. Sofia and Tom were photographed together the night of the party. Insider reports that fellow actor Will Smith then invited Sofia to a pre-Oscar party which Tom would be attending.
“She was dazzled by Tom’s megawatt smile and amused by the blizzard of phone calls, flowers and chocolates that followed their first meeting,” wrote author Andrew Morton in a New York Post article. Unfortunately, the good times didn’t last and they broke up.
