Join Anna, Sim, and Colton as they chat with today’s first caller: Madison, 26, calling in all the way from Canada to discuss a guy that she matched with on an app and met while on vacation in Hawaii. After spending one incredibly romantic night together before Madison flew home, the two have stayed in touch, leaving Madison wondering if this long-distance love interest could become more… And you don’t want to miss the surprise celebrity guests joining Anna and Sim to chat with today’s second caller: Jess, 25, from Sacremento, explains that her and her boyfriend are ready to get engaged, plan a wedding, and start a family…but every time Jess’s boyfriend is close to popping the question, one of Jess’s siblings steals his thunder by getting engaged first! Should Jess and her boyfriend’s marital bliss take a backseat to her siblings?