What Really Happened Between Janet Jackson And Matthew McConaughey

Matthew McConaughey boasted quite a dating resume during his time as a bachelor. Actors such as Sandra Bullock, Ashley Judd, Renée Zellweger, and Penelope Cruz were among the women who dated McConaughey, per Fox News. He made headlines for these relationships, but the "Interstellar" star did not make headlines for slandering his exes. For instance, McConaughey looked back fondly on his time with Cruz. "What I really love about her is that she sees everything for the first time, every time. And she's one of the best listeners I've ever met," he said in 2015 (via the Daily Mail). Cruz was among a list of exes that McConaughey once worked with, but he insisted that the romances blossomed after filming wrapped. "I've always tried to keep it professional and the people I've worked with I must say did as well," he said on "The Howard Stern Show" in 2020 (via InStyle).

While Janet Jackson's dating resume may lack the star power of McConaughey's, she has still been romantically linked to notable figures. In the '80s, she dated recording artist James DeBarge, and the two were briefly married, per the Mirror. Years later, the "Rhythm Nation" singer was rumored to be dating producer Jermaine Dupri. The two had collaborated on projects, and went public with their relationship when they showed up to the 2008 Grammys together.

Jackson met another beau — McConaughey — at the Grammys a few years earlier. Keep reading to find out more about their relationship!

Matthew McConaughey and Janet Jackson first met at the 2002 Grammy Awards. Rumors circulated that the actor and pop star were dating, but McConaughey deflected the reports and claimed the two were "just friends," per ET Online. But more tea would surface. Reportedly, the duo exchanged numbers after talking music and hitting it off at the show. The "Fool's Gold" actor described Jackson as a "dear lady" at the time, per The Telegraph. 

Jackson was the first to admit that the two dated, but not until long after, the romance had fizzled. "I guess we did date," she told Upscale magazine (via Marie Claire). Apparently, the short span of the relationship kept the singer from previously discussing it. "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," Jackson said.

McConaughey finally came clean about dating Jackson in 2019. While appearing on an episode of "Watch What Happens Live with Andy Cohen," the actor was asked to "confirm or deny" a past relationship with Jackson. After breaking out in laughter, McConaughey did relent and admitted to a very short fling with the pop superstar. "We went and had dinner, one night ... That was sorta it," he told Andy Cohen. Years after their brief romance, both McConaughey and Jackson ended up getting married. Here's more.

After dating a slew of women in Hollywood, Matthew McConaughey settled down and married model Camila Alves in 2012. The "Dallas Buyers Club" star remembers the first time he laid eyes on his future wife with clarity. "The first time I saw her walk across the room, I didn't say, 'Who is that?' I said, 'What is that?," the actor recalled in his book "Matthew McConaughey: The Biography" (via Fox News). "From that night, I haven't been on a date with anyone else," he added.

McConaughey claims he was an eligible bachelor when he met Alves. "I was very happily single and healthily single," he told People in 2016 when reflecting on the night the two met. Various media outlets have pointed out, however, that the time McConaughey met Alves (in 2006) overlaps with the period he dated Penelope Cruz. That said, the actor is on the record as not having bad blood with Cruz, nor anyone he dated in the past. "I don't dislike any of my exes," he told Elle in 2013.

Meanwhile, Janet Jackson tied the knot the same year as McConaughey when she married Wissam Al Mana in 2012. The couple was together until 2017 when they decided to call it quits which was only a few months after Jackson gave birth to their son Eissa, per People. Although the former couple had a strained relationship following their divorce they continued to co-parent their son together.