What Matthew McConaughey's Exes Have Said About Him

Matthew McConaughey may insist that he never dates his co-stars, but his romantic history suggests otherwise. Before settling down with Camila Alves, McConaughey had his fair share of relationships and flings with leading ladies like Ashley Judd, Sandra Bullock, Penelope Cruz, and even Janet Jackson (yup, they were totally a thing). Remarkably, none of his former flames have ever aired any dirty laundry about him.

This lack of drama could probably stem from how McConaughey views his past relationships. He once shared with Elle a perspective that might explain why he's managed to keep things so amicable with most of his former partners. "I don't dislike any of my exes," he said. "If I took time to form a relationship, it's gonna hurt when we move on, but are you puttin' Wite-Out over all that beautiful time together? That was real time in your life. It's connected to where you are today."

Given his no-burning-of-bridges philosophy, it's no wonder his exes haven't turned into foes. Who needs messy breakups when you can be pals with your past loves? In fact, more celebrities should be taking a page out of McConaughey's book. Here's the scoop of some of his alleged romantic relationships, including exes that have given him glowing endorsements.

Ashley Judd and Matthew McConaughey first crossed paths on the set of the 1996 legal drama "A Time to Kill," in which they played husband and wife. That didn't quite translate in real life, but they did strike a brief but headline-grabbing romance. Their relationship timeline is a bit murky as neither party has publicly delved into the specifics, but they notably made a splash — literally and figuratively — when rumors surfaced of their purported skinny dipping session in a hot tub. Judd was less than thrilled about being the subject of tabloid gossip. "There has to be a break in this culture of celebrity — it has to abate," she told The Los Angeles Times. "I'm really glad these things didn't happen to me when I was 18 or 22. We saw what Julia [Roberts] went through. She was like the sacrificial lamb, in a way."

Their whirlwind romance eventually fizzled out, and the reasons behind their split remain a mystery. Maybe the relentless media scrutiny was too much to bear? The "Kiss the Girls" star then moved on to date singer Michael Bolton but confirmed to the outlet that she and McConaughey had maintained a friendship.

Much like Ashley Judd, Matthew McConaughey met Sandra Bullock on the set of "A Time to Kill." After his fling with Judd, McConaughey entered a relationship with Bullock, and they managed to date for two years with barely anyone hearing a peep about it. It wasn't quite love at first sight, but Bullock quickly became one of McConaughey's first cheerleaders when he was still an industry underdog. Despite his not being the first choice for the film's lead, Bullock saw his star potential and didn't hesitate to throw her support behind him. "I said, 'If it's a strong, honest actor, it's my privilege to be opposite him.' I know Kevin [Spacey] and Samuel [L. Jackson] felt privileged," she told Rolling Stone. "Matthew is incredibly grounded, and anyone who is around him feels it." She added, "People keep saying, 'Hollywood is going to take him by storm.' I think it's the other way around. And Matthew will do it right."

And he did, of course! McConaughey eventually became one of Hollywood's elite, proving that Bullock's bet was spot on. Though the two never made it to the altar, Bullock and McConaughey forged an enduring friendship. "It's the work we both put in. There's a great amount of respect and love. I feel very cared for by Matthew," she shared with Cosmopolitan. "No matter where he is in his life or where I am in mine — he could be married — I know we would stay close."

After parting ways with Sandra Bullock, Matthew McConaughey was linked with actor Salli Richardson when the two showed up at the premiere of "The Wedding Planner." No official confirmation came, but hey, showing up together on the red carpet hand in hand? That's enough confirmation for us! The following year, he was also rumored to have romanced Janet Jackson, but neither of them would directly admit that. Apparently, it's because they're part of the long list of celebrity couples who never made it past the first date.

The two reportedly met at the 2002 Grammys and hit it off instantly, although McConaughey insisted at the time that their relationship was completely platonic. "We swapped some good music and she's a dear lady. She's a sweetheart but we're not dating, we're just friends," he told Upscale Magazine (via The Telegraph). Jackson, however, had a slightly different take, admitting that they were once an item. "I guess we did [date]," she dished. "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."

McConaughey shed more light on the true nature of their fling in a 2019 guest appearance on "Watch What Happens Live," when he was put on the hot seat by Andy Cohen during the "Plead the Fifth" game. The actor couldn't help but laugh at the question, but he did give us the scoop. "We went and had dinner one night," he said. "That was sort of it, yeah."

Before Matthew McConaughey got with his wife Camila Alves, he was first smitten with Penelope Cruz, whom he met on the set of the film "Sahara." They were largely private, though, with Cruz saying that she didn't want outside parties to interfere with their relationship, especially since they were both public figures. "I have no problems in recognizing I have something with Matthew, because there's nothing to hide," she shared with Mexican newspaper Reforma, according to Trib Live. "But it is something I prefer not to talk about because it always ends up coming back against you." She did share, however, that they were just friends, but their relationship blossomed unexpectedly into something more. "We became good friends and a month later it is something different. I think it's part of the mystery of love," she explained. "I can't explain these things."

They didn't last long, though, with the two succumbing to the classic celebrity relationship killer — conflicting schedules. Their joint statement to People at the time noted that they " mutually decided four weeks ago that separating was the best thing to do at this time." 

Not long after, McConaughey met Alves, and the rest, as they say, is history. Meanwhile, Cruz found love with Javier Bardem, with whom she shares two children.

Matthew McConaughey's public persona might paint him as a bit of a ladies' man, but his dating history isn't quite as scandalous as one might think, especially when he shot to fame. One Reddit user, however, dished that before he became a star, the actor made a bad lasting impression on the family of one of his exes. "My aunt dated Matthew McConaughey before he was famous. He ended up getting invited to her wedding to my 'normal' uncle, and proceeded to pass out drunk in the back of my family's car. He refused to leave, and now my dad refuses to watch his movies!" they dished.

Of course, there's no way of verifying this story, but it fits nicely with McConaughey's somewhat wild history. In 1999, his neighbors reported him for being too loud, leading to an arrest that found him naked, playing bongos, and supposedly under the influence. He never denied this, but he doesn't exactly want to erase it from his past, either. "What's wrong with beating on your drums in your birthday suit? I have no regrets about the way I got there," he told Playboy. "But what's the lesson? Shut the window that has the beautiful scent of jasmine blowing in because it's two in the morning and you might wake a neighbor."