He’s an Oscar-winning actor. She’s a Grammy-winner singer. And Hollywood was naturally the place where they crossed paths. Back in the early 2000s, Janet Jackson and Matthew McConaughey met and ended up dating… or at least going on a date. Either way, they kept their romance a secret until years later, when both of them admitted, in their own way, that they had a brief fling.
Both Jackson and McConaughey have since moved on to new relationships, but back in 2002, they met at a major entertainment event and kicked off dating rumors that would long go unconfirmed. Read on to find out more.
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According to Entertainment Tonight, Jackson and McConaughey met at the Grammys in February 2002. The pop star and actor presented the award for Album of the Year along with Gloria Estefan. The award went to the soundtrack for the 2000 film O Brother, Where Art Thou?.
It was a big Grammys for Jackson. She was nominated at that year’s show for Best Female Pop Vocal Performance for “Someone to Call My Lover” and Best Pop Vocal Album for All for You. She won the award for Best Dance Recording for “All for You” and also received the Record Academy’s Governors Award.
In 2002, amid rumors that they were interested in each other, Salon reported that McConaughey denied dating Jackson and said that they were “just friends.”
“I met her at the Grammys and found her to be a very, very sweet lady,” he told the press, according to Salon. “We swapped some good music, and she’s a dear lady. She’s a sweetheart, but we’re not dating. We’re just friends. That’s about all there is right now.”
In 2006, Jackson reportedly told Upscale magazine that she and McConaughey did date, but that their romance was short-lived.
“I guess we did date,” she said (via TheTalko). “He is a great guy and such a sweetheart. It was just for a minute, that’s why I am so hesitant to mention it.”
That same year, McConaughey and Jackson reunited at the 2006 ESPY Awards and were photographed together on the red carpet.
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McConaughey appeared on an episode of Watch What Happens Live in 2019 and played the game “Plead the Fifth” in which he was asked to answer tough personal questions. When he was asked to confirm or deny whether he dated Jackson, the Interstellar star laughed for a long time and then said, “You got the answer from that, didn’t you?” Host Andy Cohen responded, “Did I? Oh, the answer is, it didn’t happen?” McConaughey then said, “We went and had dinner one night … That was sorta it.”
After their fling, or date, or whatever it was, Jackson and McConaughey began new relationships with other people. Jackson dated music producer Jermaine Dupri from 2002 to 2009. She then married her third husband, businessperson Wissam Al Mana, in 2012, and they welcomed a son together. Jackson and Al Mana split in 2017. She had previously married singer James DeBarge in 1984, and they were together for a little over a year until their marriage was annulled. She then was married to musician René Elizondo Jr. from 1991 until he filed for divorce in 2000. Their divorce was finalized in 2003.
As for McConaughey, he began dating his wife, model Camila Alves, in 2006, and they got married in 2012. The couple have three children together.
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