Ready to Love

Overview

Ready to Love is OWN’s dating reality series about successful Black singles looking for lasting relationships. Thomas “Nephew Tommy” Miles hosts. The participants are generally in their 30s and 40s, and both men and women have a say in who remains in the dating group. The series began in 2018. Each city brings a different group of singles, with first impressions followed by conversations about compatibility, communication, family, values and future plans. The format follows adults deciding whether an attraction could become a relationship outside the mixers and dates. The Chicago chapter was announced to begin October 2, 2026 at 8 p.m. ET/PT on OWN. It is the franchise’s first Chicago season and introduces its first brother-and-sister pair. In an official preview, Tommy asks the siblings to keep their family connection from the other singles for now. The preview does not establish their final pairings or the eventual outcome of the secret. The Chicago cast includes Ashley, a 39-year-old real estate broker; Champ, a 46-year-old sports radio producer; and Jonathan, a 34-year-old facilities manager. Will Packer Media and Blink49 Studios produce the season for OWN. Where to watch in the United States: OWN is the confirmed linear broadcast home. Specific on-demand availability and a day-and-date streaming schedule for the Chicago episodes have not been verified.