Caitlyn and Alan met by pure luck on a weeknight at the infamous dive bar, The Iron Horse NYC. Caitlyn recalls that she saw a handsome guy standing alone at the bar so "she pounced". Alan debates that portion of the story. However, they both agree that they spent the remainder of the evening talking to one another. They went on their first date the following weekend and the rest is history!
Alan popped the question while vacationing with Caitlyn in St. Lucia. He had the ring, he got down on one knee and completely shocked Caitlyn! She said "Yes!"