Left to right Ashley Tarver and Kiara Poole Chicago is taking center stage in the search for love as OWN’s hit dating series Ready to Love heads to the Windy City for the first time. Season 12 premiered Friday, October 2, 2026, introducing 20 successful Black singles in their 30s and 40s who are ready to explore new connections and find meaningful, lasting relationships. Hosted by comedian and relationship expert Thomas “Nephew Tommy” Miles, Ready to Love: Chicago brings toge