OWN’s ‘Ready to Love’ heads to Chicago for new season premiering Oct. 2

OWN’s hit dating series Ready to Love will debut a new season set in Chicago on Friday, Oct. 2 at 8 p.m. ET/PT, the network announced.

The long‑running franchise follows successful Black singles in their 30s and 40s as they search for meaningful relationships in one of America’s most dynamic cities.

The Chicago season marks the first time the series has filmed in the Midwest.

Nephew Tommy Returns as Host

Comedian and relationship expert Thomas “Nephew Tommy” Miles will return to guide the cast through the dating process. The show has earned a loyal audience for its authentic portrayal of modern dating and Black relationships.

Moreover, the new season features a diverse group of professionals, including entrepreneurs, executives, attorneys, creatives and community leaders.

Ready to Love Chicago  Introduces First‑Ever Sibling Duo

For the first time in the show’s history, siblings will join the cast together, navigating the experience side by side. The season will explore how family dynamics shape dating choices and long‑term compatibility.

Singles Confront Compatibility and Communication

Throughout the season, Miles encourages participants to look beyond first impressions and focus on qualities that build lasting partnerships. The cast will engage in candid conversations about communication, values, family expectations and future goals.

Additionally, the season promises unexpected twists as the singles decide whether they are truly ready for love.

Fans Can Join the Conversation

OWN encourages viewers to follow the season using #ReadyToLove and access exclusive content on Facebook, Instagram, X and YouTube. The series is produced by Will Packer Media and Blink49 Studios.