Owen Wilson – 52
Owen Wilson may not be the typical dashing leading man that fans often see in movies, but his charm and quirky antics make up for it! He has starred in various blockbuster flicks like Zoolander and Wedding Crashers throughout the years, but unlike his career, Owen hasn’t been that lucky in the love department.
To date, the comedian had two serious and long-term relationships, which gave him two sons. That would’ve been enough for some to settle down, yet it never seemed to work out for any of Owen’s former girlfriends. Oh well, maybe he’s just not the marrying type.
