Sandra Bullock and Ex Jesse James' Relationship Timeline

Out of all the iconic love stories in Hollywood, we can’t forget about Sandra Bullock and her ex-husband, Jesse James. A timeline of the former couple’s romance proves their relationship was filled with highs, lows and plenty of memories.

The Blind Side star and the Monster Garage host first met in 2003. After hitting it off, Sandra and Jesse started dating and quickly fell in love. The Hollywood stars were married by 2005.

Throughout the first few years of their marriage, Sandra and her handsome hunk looked happier than ever as they attended red carpet events together. Jesse also supported his successful spouse as she won countless awards thanks to her incredible talents as an actress.

It was Sandra, however, who praised her hubby for standing by her side as she accepted the Academy Award for Best Actress in 2010. “To my husband, there is no surprise that my work got better when I met you because I never knew what it felt like for someone to have my back,” she gushed on stage.

Sadly, the Speed alum and Jesse’s relationship started to crumble when reports of multiple alleged affairs surfaced that same year. After just months of public scrutiny, the Miss Congeniality actress filed for divorce. Around the same time, she adopted her eldest son, Louis.

Looking back, Sandra “never thought she’d get past the heartbreaking and humiliating breakup with Jesse,” a friend close to the Proposal star told Closer Weekly in December 2019. “Sandra has been through hell.”

Fortunately, that all changed when she crossed paths with her current beau, Bryan Randall, in 2015. “Meeting him was literally a godsend,” the insider sweetly added.

Aside from sharing one of the “most solid” bonds in Hollywood, Sandra and Bryan are also crushing it at raising the brunette beauty’s son, Louis, as well as her daughter, Laila, whom she adopted in 2015.

“The kids are growing up so fast and Bryan couldn’t be more involved in their upbringing,” a separate source told Closer. “The kids adore Bryan and of course, Sandra still pinches herself that she’s been so lucky finding Bryan.”

Fans can’t wait for the day the lovebirds finally tie the knot!

In the meantime, scroll through the gallery below to see a timeline of Sandra and Jesse’s relationship over the years.

2003

The former couple met when Sandra arranged for her then-10-year-old godson to meet Jesse for his birthday back in late 2003. At the time, they took a tour of Jesse’s garage, West Coast Choppers, because the youngster was a fan of the show Monster Garage. It was there that sparks flew between the two.

2007

When she married Jesse, Sandra became the loving mom of his three kids, Jesse James Jr., Chandler James and Sunny James, from previous relationships. During a press conference promoting Premonition in 2007, Sandra made a rare comment about being a stepmom.

“Here’s the thing, I have children. I married into children. I love those children. My concern and my love for those kids as a coparent is no less than if I had that child biologically,” she once said. “I don’t see the difference between that and having your own child biologically. I feel for the children I have in my life and I would not change that.”

2009

Four years into their marriage, the American entrepreneur and Sandra were granted full custody of Jesse’s daughter Sunny. This came after a months-long custody battle with Jesse’s ex-wife Janine Lindemulder, with whom he shares his youngest daughter. Sandra was helping raise Sunny after Janine was sentenced to six months in prison for tax evasion in late 2008, according to reports.

2010

Just when fans thought the pair were going strong, In Touch Weekly reported about Jesse’s alleged cheating with Michelle “Bombshell” McGee, a model who claims she had an 11-month affair with Jesse. Following the news, multiple other women came forward with stories of infidelity.

Shortly after, Jesse issued a public apology to his then-wife and his three kids. “There is only one person to blame for this whole situation, and that is me,” he said in a statement. Though a “vast majority” of the allegations made against him were “untrue and unfounded,” he noted, “it’s because of my poor judgment that I deserve everything bad that is coming my way.”

Jesse went on to say, “This has caused my wife and kids pain and embarrassment beyond comprehension and I am extremely saddened to have brought this on them. I am truly very sorry for the grief I have caused them. I hope one day they can find it in their hearts to forgive me.”

However, Sandra filed for divorce from Jesse in late April 2010 and it was finalized in late June 2010.

2015

Five years after their divorce, Sandra found love with Bryan. The couple met in 2015 after she hired the handsome hunk to come take photos at her son Louis’ birthday party. Since then, the pair has been happier than ever.

“They are best friends and partners,” a source once told Closer, adding Sandra is Bryan’s “greatest supporter.”

2017

In March 2017, Jesse addressed the cheating incident that happened over a decade ago. “Yeah, I did cheat on my wife. I stood up and took accountability for it and apologized. And that’s end of story,” he told the Daily Mail at the time. “In general, both women and men cheat. It’s part of life.”

2020

Despite being heartbroken in the past, Sandra is looking forward to her future with Bryan. “Sometimes they sit back and laugh because they look at their lives and they feel like an old married couple,” another source told Closer in December 2019. “They’re set in their ways and content. The kids are healthy and happy. This is all she’s ever wanted: this is heaven for Sandra.”