Jon Stewart & Tracey McShane | 24 Years

In the late ‘90s, Jon Stewart was set up on a blind date with Tracey McShane while he was working on the Wishful Thinking movie. It must have gone great, given that three years later, he proposed. In fact, he went through the trouble of making a personalized crossword puzzle to do so.

Tracey has since published a book titled Do Unto Animals, whereas Jon has started and stopped hosting Comedy Central’s The Daily Show. They currently operate two animal sanctuaries in New Jersey, one in Colts Neck and a smaller one in Middletown. Just Jon Stewart alone is worth close to $120 million right now.