Sandra Bullock romanced some of Hollywood’s most eligible bachelors before meeting “love of [her] life” Bryan Randall.
The photographer, whom she started dating in 2015, tragically died at age 57 in August 2023 following a three-year battle with ALS.
Although the pair never married, Bullock previously tied the knot with Jesse James in 2005.
The former couple called it quits five years after saying “I do,” when several woman came forward claiming they were having affairs with James. He admitted to cheating on the “Proposal” star in 2011.
Read on to find out everything you need to know about the “Bird Box” actress’ romantic life.
Tate Donovan
Bullock’s first public relationship was with “The O.C.” alum Tate Donovan, whom she met on the set of “Love Potion No. 9” in 1992.
Donovan and Bullock ended up dating for three years and even got engaged, but even though it didn’t last, he was responsible for introducing the “Miss Congeniality” star to her friend Jennifer Aniston.
“We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being,” Bullock told the “Friends” actress in a February 2020 Interview magazine cover story.
“We both partook of Tate. … Who was a very patient human being, given that he dated us both,” she joked.
Troy Aikman
The “Lost City” star never confirmed her romance with former Dallas Cowboys quarterback Troy Aikman, however the pair were first linked in 1995.
The two also reportedly had a brief rekindling in 2014 following her divorce from James.
Matthew McConaughey
One of her most high profile boyfriends was her “A Time To Kill” co-star Matthew McConaughey.
The pair were secretly dating from 1996 to 1998, and only spoke about the relationship after they called it quits.
“It’s the work we both put in. There’s a great amount of respect and love,” she told Cosmopolitan in 2003.
“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,” she explained.
The duo have remained friendly through the years, with Bullock counting McConaughey’s wife, Camila Alves, as one of her pals.
Bob Schneider
The “Blind Side” Oscar nominee dated musician Bob Schneider from 1999 to 2001, but little is known about their relationship.
“As celebrities go, Bob and I have a very low-key relationship,” she told Cinema.com in 2000, referencing the country singer.
“It’s something I learned through trial and error,” she went on.
Ryan Gosling
Bullock has played coy when asked about her short-lived relationship with Hollywood heartthrob Ryan Gosling.
When a Cosmopolitan reporter questioned whether she and Gosling were “just friends” in a 2003 interview, she responded, “If you were to add the word ‘just,’ it would probably be a bit of a lie. So I’d say we’re friends.
The “La La Land” actor, for his part, referred to his ex as one of the “greatest girlfriends of all time,” during a 2011 interview with The Times
Jesse James
The “Ocean’s 8” star star met the West Coast Choppers founder while visiting the set of his show “Monster Garage.”
Following several ups and downs throughout their marriage — which lasted from 2005 to 2010 — things came to a head when Bullock discovered James’ infidelity.
He later admitted to being unfaithful throughout their relationship.
“Yeah, I did cheat on my wife, yeah,” he 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,” he went on.
Though Bullock and James initiated the process to adopt a baby boy named Louis together in January 2010, she finished the process as a single parent after their split.
She also adopted her daughter, Laila, in December 2015.
Chris Evans
Bullock and “Captain America” star Chris Evans, who is 17 years her junior, first met at the Vanity Fair Oscars party in 2012.
He then revealed Bullock used to be his childhood crush.
“I used to be in love with Sandra Bullock when I was growing up. Sandy B. was my girl,” he told Playboy at the time.
“I remember seeing ‘Speed’ when I was in seventh grade and just thinking, ‘that’s her.’”
The pair may have dated two years later, however it remains unclear exactly what their relationship status was.
“They are not in a relationship, but they are definitely hanging out and are in the early getting-to-know-each-other phase. They haven’t put a title on it, but they really like each other,” a source claimed to E! News in May 2014.
Bryan Randall
Randall met Bullock in January 2015 when he was hired to take photos at her son, Louis’ birthday party.
Their relationship quickly became romantic, and they attended Aniston’s wedding to Justin Theroux’s together that August.
They even made their red carpet debut as a couple at the premiere of her 2015 film “Our Brand Is Crisis.”
“I found the love of my life,” Bullock gushed in a December 2021 episode of “Red Table Talk.”
“We share two beautiful children — three children, his older daughter. It’s the best thing ever.”
He died “peacefully” on Aug. 5, 2023 after a “three-year battle with ALS,” his family said in a statement to Page Six.
“Bryan chose early to keep his journey with ALS private, and those of us who cared for him did our best to honor his request,” they continued.
“We are immensely grateful to the tireless doctors who navigated the landscape of this illness with us and to the astounding nurses who became our roommates, often sacrificing their own families to be with ours,” the family continued, asking for “privacy to grieve and to come to terms with the impossibility of saying goodbye to Bryan.”
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