Kris Jenner and Bruce Jenner
The Kardashian matriarch Kris Jenner and former Olympian Bruce Jenner got hitched in 1991 and have two daughters together, Kendall and Kylie. It seems like the split has been beneficial to the entire family however; Bruce's son Brody recently said that his father's marriage to Kris caused a lot of heartache to Brody and his siblings growing up. Kris has been spending time with the much-younger Ben Flajnik and lately Bruce has been sporting a ponytail. Everybody wins!