She also dated Edward Norton in 1996 and Luke Wilson in 1999. Off all the short term relationship that she had, her relationship with Fabrizio Moretti was the longest.
Drew and Edward Norton at the Oscars, Source: E online
They started dating in 2002 and their relationship ended in 2007. Drew herself admitted about the duration of her relationship and in an interview to the Harper's Bazar she stated,
"The longest I've ever been with someone was like two to three years, so I'm in uncharted waters, right now I'm more into championing him as a human being than gushing love for him."
After her break-up with him, she started an affair with American actor Justin Long in 2007. They rekindled their love with each other two times as they break-up in 2008 but then patched it up again in 2009.
Drew with Justin Long- During a Film Shooting, Source: Daily Mail
The couple was very happy after their marriage and they were expecting way too much from their marriage. After their marriage Drew said,
“I want our kids to have someone to roll their eyes with when Mom and Dad are being totally lame and goofy,”
But it seems that they didn't get any chance to raise children as they divorced after three years of marriage. They filed for a divorce in 2001, and after the divorce, Tom released his statement stating,
“Drew is a wonderful woman. I love her very much. I wish our marriage could have worked out. I wish her much happiness.”
After the heartbreaking divorce two times in a row, Drew was not ready for any commitment anytime soon.