Cindy Crawford and Rande Gerber – 22 years

American Supermodel Cindy Crawford was once famously married to actor Richard Gere, but that clearly didn’t work out since she’s now been with businessman Rande Gerber for 20 years. Rande had been Cindy’s friend for quite some time before they started dating, until she finally made the decision to let him out of the friend zone and things turned out wonderfully.

Cindy Crawford and Rande Gerber got hitched in 1998. When Gerber was asked about their relationship in an interview, he said that the secret to their success was maintaining their friendship. “You have to just keep that friendship and fun in the relationship,” he explained.