Rachel Zoe & Rodger Berman – 22 Years
In 1991, at the age of 19, Rachel Zoe fell in love with Rodger Berman, who was 25 years her senior. When they first met, the pair was both employed in restaurants.

“I recall the first time I saw her, wearing a tight black mini dress, high-heeled pumps, stick-straight hair, and big red M.A.C. Chili lipstick (her trademark),” he recalled. “She was the most gorgeous woman I’d ever seen.” They’ve since had two children.