Sandra Bullock Dated These 8 Men Before Bryan Randall: Tate Donovan, Jesse James, Chris Evans and More

Sandra Bullock and Tate Donovan crossed paths when they worked together in the film Love Potion No. 9. They got engaged after dating for three years but broke up in 1995, according to Cosmopolitan.

The former couple never spoke about the reason behind their split, but the Miss Congeniality actress revealed in an interview with Vanity Fair in 1995 that some things did not end well between them.

"I can't explain why things worked out the way they did," she said. "We both know why it happened."

Bullock soon dated the former Dallas Cowboys quarterback Troy Aikman in 1995. Although they ended their relationship then, they reconciled and were linked again in 2014 following The Proposal star's divorce from Jesse James.

Months after her split from Aikman, Bullock started seeing A Time to Kill film technician Don Padilla.

She revealed in 1996 that she had been dating for 10 months but didn't specifically name him at the time. She later attended The Net premiere with the film tech.

However, a 1997 Rolling Stone profile of the actress revealed that Bullock had issues on the set of A Time to Kill amid her impending breakup with her then-beau.

Bullock and Matthew McConaughey managed to hide their relationship from the public, making people only know they were a thing only after everything was over.

The duo remained friends even after ending their two-year relationship. Bullock also got the chance to befriend his wife, Camila Alves.

"It's the work we both put in," she told Cosmopolitan in 2003 when asked how they stayed friends after the split. "There's a great amount of respect and love. I feel very cared for by Matthew. No matter where he is in his life or where I am in mine — he could be married — I know we would stay close."

The 59-year-old marked another two-year relationship in the past with country singer Bob Schneider. Like her previous relationships, Bullock wanted to keep things as private as possible.

"As celebrities go, Bob and I have a very low-key relationship," she told Cinema.com. "We live our life together one day at a time. It's something I learned through trial and error."

Ryan Gosling and Bullock went from being costars to boyfriend-girlfriend from 2002 to 2003.

Although their relationship was brief, the La La Land star revealed in his 2011 interview with The Times (via Us Weekly) that Bullock was one of the "greatest girlfriends of all time."

Bullock met Jesse James while touring the set of his show, Monster Garage.

The then-couple tied the knot in 2005 after they started dating, but their marriage life was tested when the allegations about the West Coast Choppers founder's infidelity emerged. Per reports, he cheated on the actress with multiple women.

James and Bullock finalized their divorce in June 2010, and he admitted he stepped on his marriage.

"Yeah, I did cheat on my wife, yeah," James told the Daily Mail in 2017. "I stood up and took accountability for it and apologized. And that's [the] end of story. In general, both women and men cheat. It's part of life."

It took Bullock several years before sparking new relationship rumors.

The actress and Captain America actor Chris Evans became the subject of dating buzz in 2014, two years after they first met at a Vanity Fair Oscars party. At that time, a source told Us Weekly that the actor was pursuing Bullock.

In response to the reports, the While You Were Sleeping actress quipped about her connection to Evans, saying they got married and everyone was "a little behind."

"We filed for divorce, and I hope everyone can respect our privacy," she joked. "But we're going to remain friends and share responsibility of the farm animals we've taken on because you just can't abandon the animals."

Meanwhile, Evans confessed to Playboy how he used to be in love with Bullock as a child.