[custom_adv] 12. Matthew Perry - Age 46 Matthew "Chandler Bing" Perry dated actresses Julia Roberts, Yasmine Bleeth, and Lauren Graham. He was in a relationship with younger actress Lizzy Caplan from 2006-2012, but never married. [custom_adv] 11. Owen Wilson - Age 47 Comic actor Owen Wilson has dated several A-list celebrities, including Sheryl Crow and Kate Hudson, to whom he was engaged in 2008. He has a son with ex-girlfriend Jade Duell, born 2011, and another son with his personal trainer, born 2014. [custom_adv] 10. John Cusack - Age 49 John Cusack has managed to date several famous actresses while keeping the relationships out of the spotlight. The actor has been involved with Neve Campbell, Minnie Driver, and his Say Anything co-star Lili Taylor. [custom_adv] 9. Matt Dillon - Age 51 Despite a public relationship with Cameron Diaz in the late '90s, leading man Matt Dillon never married. [custom_adv] 8. Sheryl Crow - Age 53 Musician Sheryl Crow has never been married, but she has had relationships with some of the biggest names in film, music, and sports. Crow has been notably involved with actor Owen Wilson, musician Eric Clapton, and cyclist Lance Armstrong. [custom_adv] 7. Hugh Grant - Age 55 Charming bumbling actor Hugh Grant never took the leap. He had a 13-year relationship with model/actress Elizabeth Hurley, and he is the godfather of Hurley's child. Grant has a child of his own with Tinglan Hong, a woman with whom he reportedly had a brief affair. [custom_adv] 6. Tim Robbins - Age 57 Tim Robbins has never been married, although he had two children and a 20-year relationship with Susan Sarandon. Sarandon was married previously to actor Chris Sarandon. [custom_adv] 5. Oprah Winfrey - Age 61 Oprah Winfrey has never been married, though she has been dating her partner Stedman Graham for over 25 years. Winfrey also dated Roger Ebert in the mid-80s. [custom_adv] 4. Condoleeza Rice - Age 61 Former Secretary of State Condoleeza Rice has never been married. Rice was engaged to NFL player Rick Upchurch in the 70s, but the relationship didn't work out. [custom_adv] 3. Alan Rickman - Age 69 Alan Rickman has lived with his girlfriend, Labour party councillor Rima Horton, since 1977, but they are not married. They have been together since 1965, when they were 18 and 19. [custom_adv] 2. Al Pacino - Age 75 Al Pacino may have three children, but the Godfather star has never been married. Pacino has one child with acting coach Jan Tarrant and two with Vacation actress Beverly D'Angelo. He has also dated Diane Keaton, Tuesday Weld, Jill Clayburgh, Marthe Keller, Kathleen Quinlan, and Lyndall Hobbs. [custom_adv] 1. Coco Chanel - Age 88 Designer Coco Chanel never married. She also did not have any children.
