Owen Wilson, Age 51 – Unclear

Looking at Owen Wilson’s dating life, things get pretty confusing pretty quickly. He has kept on and off relationships with most of his exes, and even though he was never married to any of them, he has a total of three children, all from different mothers.

One of his most lengthy relationships has been the one he was in with Kate Hudson, with whom they spent about three years on and off, but incredibly off the radar, after they met on You, Me and Dupree. That was even before he met with his baby-mother Caroline Lindqvist, with whom they’ve also been on and off reportedly since 2003.