Skyler Scott Caplinger was born Skyler Scott Leffingwell on April 1st, 1995 in Upland, IN. He was featured on Netflix's Original Series 'Say I Do: Surprise Weddings' as the season's final couple, alongside his now husband, Randy Caplinger. During the finale episode, Skyler surprises Randy with a "re-proposal" and with the help of the 3 experts, Jeremiah Brent, Thai Nguyen, and Gabriele Bertaccini, gift him the wedding of their dreams.