Matt repeatedly denied that he was engaged to Odessa, whom he dated from about March of 2001 (or possibly before) until the official end of the relationship in October 2003, although they appeared to separate for most purposes in about January 2003.
Odessa, who was originally from Black Mountain, North Carolina, met Matt on the set of All The Pretty Horses in 1999, when she was working as Billy Bob Thornton's driver. Odessa later became Billy Bob's assistant, and became part of Matt's circle of friends in LA. Matt introduced her to Ben Affleck, and she later became Ben's assistant, including during his pre and post-rehab period.
True fact: Matt and Odessa 'officially' only appeared in public together on two occasions - the international premieres for The Bourne Identity in Taipei, Taiwan and Sydney, Australia.
Here's the long version of the story...
It is still reported that Matt 'dumped' then girlfriend Minnie Driver on the Oprah Winfrey show when promoting Good Will Hunting in January 1998. This is incorrect, as Matt has repeatedly stated.
On the program Matt said that he and Minnie are no longer together, or involved in a romantic sense, and that the split had been amicable. Minnie was not backstage, and did not appear on the program.
The Golden Globes were held a few weeks later, and by this stage Oprah had probably been broadcast, and the breakup was public knowledge. Perhaps because Matt was already seeing Winona Ryder by this stage (but not publicly), or maybe after comments by Minnie, the media started to write stories that she was dumped on Oprah. I think the main point is that Minnie did not dissuade the rumors, and probably played them up.
By the Oscars, she was definitely being viewed as the 'wronged woman', and made a few comments that supported the 'dumping' theory. A story after the Oscars and reported on Mr Showbiz was the first to support Matt, when 'friends' called the reporter up and said Matt had done everything possible to make it easier on Minnie during the ceremony (avoiding her etc), that he had done nothing wrong, and that it was Minnie being difficult.
Here's that report, from early August 1998:
Matt on Minnie Defensive?
Can you handle still more about the now-ancient breakup of Minnie Driver and Matt Damon? Minnie, as you know, has made little attempt to hide her bitter feelings about the split, but now friends of the Saving Private Ryan star have decided to come to his defense. Of course, these friends also wish to remain anonymous, so this information should be taken with the requisite boulder of salt.
The New York Post's Page Six reports that Matt is "sick and tired" of his Good Will Hunting co-star telling the story of how he allegedly dumped her on The Oprah Winfrey Show. Driver, out plugging The Governess, has recently talked openly of the breakup with Cosmopolitan and the Los Angeles Times, among others, and that has Matt's friends fuming. They claim reports of his cold and loutish behavior simply aren't true.
"Minnie Driver is talking her head off," says one unidentified friend of Damon's. "She keeps accusing him of breaking up with her on Oprah Winfrey. And that was bad. He made a huge mistake; he blurted out the truth. But she knew about the breakup for a least a week, probably 10 days before Oprah."
The actress told the Times last week, "Everything has to be made so mythic.. I had to be the victim. It's horrendous breaking up with someone anyway, but to have it be so public and to be cast in a role that would never play if they were paying me-this wronged woman." She added, "It's unfortunate that Matt went on Oprah. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate."
Minnie's sister recently told Cosmo that the relationship ended before the show, which Matt's friend says is further evidence of the actress's betrayal. "Her own sister called her a liar," says the insider.
And what of reports of the arctic chill between the former lovers at the Oscars, where winner Matt was spotted post-ceremony with new squeeze Winona Ryder? Or the obvious tension between the two at the ShoWest Awards, where Minnie was crowned Female Star of Tomorrow, with Matt receiving the male equivalent. "It was pretty strange," Driver told the Times, "being the counterpart to the person you used to be with-the male and female equivalent of each other, you're standing on the stage with someone who's not even speaking to you anymore. That was pretty bizarre. There had to be some reality check there. It was weird, uncomfortable, sad and strange. I really wanted to enjoy it more than I did."
But the friend tells the paper that Minnie wanted Matt to avoid her. "She and Matt have the same agent," says the source. "She called [the agent] up before the Academy Awards, and he said, 'Matt will do whatever you want to make it easier.' And she said it would be better if they didn't meet face to face in public. Matt's not talking to her was a direct request." [End of story]
In the "Cosmopolitan" magazine interview mentioned above, Minnie definitely made out that she was the wronged one, and did nothing to suggest otherwise. The denial by her sister Kate was never widely reported by the media.
Matt didn't deny or comment on the TV dumping rumors until the GQ interview to promote Ripley in December 1999.
Here's the quote:
Part of his radio silence stems from lessons he learned after being more open about his romance with Claire Danes and his fandango with Minnie Driver. During the run-up to the 1998 Academy Awards, Damon admitted on Oprah that he and Driver were no longer an item. Driver in turn did a series of interviews in which she portrayed Damon as a cad for breaking-up with her on daytime television. "That was just false," he says now. "It's something I've never talked about publicly, but we broke up three weeks before that. It's hard not to respond when you feel like you're getting smoked in public."
From the Ripley premiere in late 1999:
You ought to stay away from Oprah. People still think you cruelly dumped Minnie Driver the last time you were on her show.
"Well, people generally have whatever impression the media gives them, but things are very different when you're on the inside."
From Glamour magazine, October 2002:
It's hardly surprising that he's still upset over the 'love-rat' label that stuck to him when he supposedly dumped Minnie Driver on Oprah. He flushes when reminded, but more out of annoyance than embarrassment. It's hard to picture him - down to earth, family-oriented - being such a cad. "It's weird that I still get asked this, because Minnie debunked the myth [by admitting they'd already split] a couple of years ago. I really don't know where it came from. But no," he screws his face up in distaste, "I"m not like that. It's not something I would ever do. And it was a bummer. It was the first time I'd experienced that kind of attention. It made me much more guarded about my personal life. I don't really read papers now. I'm walking around in ignorant bliss."