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The last time you thought about these couples, you were probably listening to "Womanizer" on your classic iPod.
The two dated in the early '00s and were even briefly engaged in 2003. But after breaking it off, the two have remained good friends.
Renée and Jack met on the set of their film, Cold Mountain, in 2002 and dated for about a year and a half, breaking up at the end of 2004.
Ryan and Alanis began dating in 2002 and became engaged in 2004. After five years together, the pair called off their engagement in 2007.
Ashley and Lance briefly dated in 2007. At the time, she was 21 and he was 36, and reportedly, Lance was warned by his team that dating her would ruin his credibility in the work he was doing for cancer research.
The pair dated for a little over a year after meeting on the set of their 2006 film, The Black Dahlia.
Jennifer and Vince met in 2005 on the set of their film, The Break-Up. The two dated for about a year before breaking up in real life in 2006.
Lenny and Nicole quietly dated from 2002 to 2003. She later revealed that the two had actually been engaged, too, but the timing was off, saying, "It just wasn’t right. I wasn’t ready. We weren’t ready."
Mila and Macaulay were in a long-term relationship, dating from 2002 to 2011. While the two have never really spoken about their relationship, Mila did reveal to Dax Shepard on his podcast, Armchair Expert, that the breakup was bad, saying it was a "horrible, horrible breakup."
Rumors that the unlikely duo were dating began in December 2009. But by March 2010, it appeared that things had fizzled out.