Kate Hudson and Owen Wilson
- 2006 – The two stars began dating after meeting on the set of You, Me and Dupree.
- 2007 – Kate and Owne then called it quits in June, though a source told People “they’re still friends.” In August, Owen who battles substance abuse and depression, tried to commit suicide.
- 2008 – After reuniting at an Oscar bash, the couple reconciled in February, but broke up just three months later.
- 2009 – Third time’s a charm eh? *coughs* not. The couple were back on again February, but their relationship soon fizzled out.