In this episode, Kyle is joined by his friend Chloé Fulton. Kyle and Chloé met while performing improv together in New York City. Today, they are sharing their mutual love for television. Kyle has never seen any show from the "Bachelor" franchise and he is starting with Rachel, the first African American Bachelor/Bachelorette searching for love. Chloé, a seasoned obsessor of all things Bachelor Nation, is going to help Kyle work out the quagmire of information that comes with the firsts episode of a season. Later on, they talk reboots and revivals and a friendly wager is made on the heads of Hollywood Legends.