Sandra Bullock’s dating history: From Bryan Randall to Ryan Gosling

Sandra Bullock had a series of romantic relationships with some of Hollywood's most eligible bachelors before finding love with Bryan Randall, whom she started dating in 2015. Sadly, Randall passed away at the age of 57 in August 2023 after battling ALS for three years. While Bullock never married Randall, she was previously married to Jesse James in 2005. The couple ended their marriage five years later due to James' infidelity, with multiple women coming forward claiming to have affairs with him.

James admitted to cheating on Bullock in 2011. Here is everything you need to know about Bullock's romantic life. Bullock's first public relationship was with actor Tate Donovan, whom she met on the set of the movie "Love Potion No. 9" in 1992. They dated for three years and even got engaged, but their relationship eventually ended. However, Donovan introduced Bullock to her friend Jennifer Aniston. Bullock joked about their shared connection to Donovan, saying, "We both partook of Tate...who was a very patient human being, given that he dated us both." Although Bullock never confirmed her romance with former Dallas Cowboys quarterback Troy Aikman, they were first linked in 1995. They reportedly had a brief rekindling in 2014 after Bullock's divorce from Jesse James. One of Bullock's most high-profile relationships was with her "A Time To Kill" co-star Matthew McConaughey. They secretly dated from 1996 to 1998 and spoke about their relationship after it ended. Bullock expressed her respect and love for McConaughey and said they would always remain close, regardless of their respective personal lives.

Bullock dated musician Bob Schneider from 1999 to 2001, but little is known about their relationship. She described their relationship as low-key and learned from past experiences about keeping her personal life private. Bullock played coy when asked about her relationship with actor Ryan Gosling.

When questioned about their connection, she emphasized that they were more than just friends. Gosling, in turn, praised Bullock as one of his greatest girlfriends. Bullock met Jesse James while visiting the set of his show "Monster Garage." Their marriage lasted from 2005 to 2010, but ended after Bullock discovered James' infidelity. James admitted to cheating throughout their relationship and expressed remorse for his actions. Although Bullock and James initially started the process of adopting a baby boy together, Bullock completed the adoption as a single parent after their split. She also adopted her daughter Laila in 2015. Bullock and "Captain America" star Chris Evans first met at a party in 2012. Evans admitted to having a childhood crush on Bullock and revealed that they had a close relationship. Sources claimed that they were hanging out and getting to know each other, but their exact relationship status remained unclear. Bullock met Bryan Randall in 2015 when he was hired to photograph her son's birthday party. Their relationship quickly developed into a romantic one, and they attended Jennifer Aniston's wedding together.

They made their red carpet debut as a couple at the premiere of Bullock's film "Our Brand Is Crisis." Bullock described Randall as the love of her life and expressed her happiness with their blended family. Tragically, Bryan Randall passed away in August 2023 after a three-year battle with ALS. His family requested privacy to grieve and come to terms with his loss. Bullock expressed her love and gratitude for Randall, as well as her appreciation for the doctors and nurses who cared for him.

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