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 a mutual love for television. Kyle has never seen any show from The Bachelor franchise and he started with Rachel, the first African American Bachelor or Bachelorette searching for love. Chloé, a seasoned obsessor of Bachelor Nation, is going to help Kyle work out the quagmire of information that comes with the first episode of a season. Later on, they talk reboots and revivals and a friendly wager is made on the heads of Hollywood Legends.