Sandra Bullock and Jesse James

Who

Oscar-winning actress and producer Sandra Bullock, 58, and West Coast Choppers founder and TV personality Jesse James, 53.

How They Met

Bullock reportedly gifted her motorcycle-obsessed 10-year-old godson a trip to West Coast Choppers's Long Beach headquarters for Christmas in 2003. There they met Monster Garage host James, who'd agreed to give a special tour of the shop. After the visit, Bullock returned to her office to find a missed call from James.

Suspecting that James was interested in her, she told an employee not to give him her personal number. "I said, 'Do not give the man my number — give him my email. I'll politely say, No, I'm not in a place … '" she told Vanity Fair. She turned him down once, twice, and so on until James caught her off guard with a virtual game of 20 Questions.

"I said, 'Who do you think you are? You're not in a position to play 20 Questions with me!'" she remembered. "'I am not going to answer them!' I thought they were going to be 'Do you have a chassis on your car?'"

But James surprised her and asked thoughtful questions about non-motorized topics. "So basically through a courtship of letters, which I didn't even recognize, I learned about a human being," Bullock said. "It was not something I wanted, needed, or looked for, but because he was a stronger person than I was, spiritually and on a tolerance level, I was lucky enough that he educated me."

Speaking more bluntly about her initial bias against James, Bullock told InStyle that she "assumed he was a homophobic chauvinist, a bigot who killed people."

James had preconceived notions about Bullock as well.

"I assumed she was a bitch and some Hollywood snob and didn't really give it two thoughts," James told Nightline in a 2010 interview, "and then I talked to her for a couple minutes and it was like getting hit in the head with a brick. Here's a woman I had assumptions about and she couldn't be farther from that."

After a brief courtship, James proposed to Bullock with a vintage Tiffany diamond ring from 1910 and they planned to wed the following year … in secret.

In July of 2005, the couple hosted 270 guests at a ranch in the San Ynez Valley under the guise of a celebration for Bullock's 41st birthday. Aspiring for a "vintage Western barbecue feel," Bullock walked down the aisle in satin cowboy boots and made James's wedding band herself in his shop.

Bullock told VF that she and James planned a cross-country road trip for their honeymoon but "pulled the plug" after they were followed by paparazzi.