Cindy Crawford & Rande Gerber

Cindy Crawford and Rande Gerber certainly have one of Hollywood’s most solid marriages. They have been a couple for over twenty years now, proving that they’re in it for the long haul! The business magnate met the supermodel back when she was married to Pretty Woman star Richard Gere. Before Gerber and Crawford became lovers, they were close friends— so much so that the model credits their underlying friendship for keeping their bond so strong over these years.

The couple exchanged wedding vows in a simple ceremony in the Bahamas in the late ’90s. Throughout their marriage, they have battled personal issues hand in hand and welcomed two lovely children: Kaia Jordan and Presley Walker, both of whom are now pursuing modeling careers. When asked about how they’ve kept a healthy relationship, the power duo said that having a date night from time to time is the key.