Dick Van Dyke and Arlene Silver: 46 Years
TV legend Dick Van Dyke and makeup artist Arlene Silver tied the knot in February 2012 — six years after meeting at the 2006 Screen Actors Guild Awards. At the time, the pair were 87 and 41 years old.
While at the 2013 SAGs on January 27, where he received a lifetime achievement award, Dick reminisced about his first encounter with his much younger ladylove. “[It was] the first time I ever hit on a woman in my life!" he revealed to CNN on the red carpet. "I walked up to her and said, 'Hi, I'm Dick.' I don't think she knew who I was!"