Suspicious Details About Matthew McConaughey & Sandra Bullock's Past Relationship

Sandra Bullock and Matthew McConaughey are two of the biggest stars in Hollywood, yet somehow, the pair dodged a media frenzy during their brief romance. Still, Bullock alluded to her relationship history with the "Dallas Buyers Club" actor more than once. In a 2003 interview with Cosmopolitan, the "Miss Congeniality" star said: "I have a hard time being just friends." And when the interviewer referred to McConaughey as her ex-boyfriend on multiple occasions, Bullock did not correct her. McConaughey even confirmed their relationship in a 2017 interview with Playboy (via People).

McConaughey and Bullock met on the set of the 1996 film "A Time To Kill," in which the former played Jake Brigance, a lawyer undertaking the case of a Black man who killed his daughter's rapists; the latter portrayed Ellen Roark, a law student backing Brigance as a part of his defense counsel. At the time, Bullock was coming off the success of 1994's "Speed" and 1995's "While You Were Sleeping," and was considered a star. But for McConaughey, his "A Time To Kill" role was the first time he was a lead in a movie, and it sounds like stardom went to his head. 

McConaughey did not just date one "A Time to Kill" co-star, but two. He also had a romance with Ashley Judd, who played his wife in the film (lest we forget their hot-and-heavy 1996 Interview cover). There were even rumors that the Hollywood legend was dating both Judd and Bullock at the same time. 

Matthew McConaughey has since learned to keep things friendly with his co-stars as a form of respect. "I've always tried to, you know, keep it professional," the "Interstellar" actor said on "The Howard Stern Show" in 2020. "The people I worked with, I must say, did as well. We had certain crushes on each other at certain times, but we always just kind of kept it professional."

There certainly doesn't seem to be any ill will between him and Sandra Bullock. They have even joked about their '90s romance later in life. "I've worked with you. I've tried to kiss you, successfully and unsuccessfully," he said at the 2014 "Guy's Choice" awards, adding, "So, Sandy, here is to your decade of hotness, I'm glad to say that I knew you the decade before as well." In her Cosmopolitan interview, Bullock described their friendship as timeless, admitting that "There's a great amount of respect and love."

Even though McConaughey worried he'd never find love, the actor married Camila Alves in 2012, and they share three children. Bullock was married to Jesse James from 2005 to 2010. Then in 2015, she found a longtime partner in Bryan Randall, a model who sadly died in 2023 after battling ALS for three years.