OWN’s Ready to Love Brings Chicago Singles Together for Season 12
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 together a diverse group of Chicago-area professionals whose careers, personalities, and life experiences shape their approaches to dating.
From entrepreneurs and executives to attorneys, creatives, and community leaders, the singles enter the experience with different expectations for love. As they get to know one another, they will face the realities of modern dating, including communication challenges, family dynamics, personal values, and questions about long-term compatibility.
Will Packer, executive producer and founder of Will Packer Media, says the appeal of the series comes from watching accomplished adults navigate the unexpected turns that relationships can bring.
“What makes Ready to Love so compelling is that these are grown, accomplished people who have built full lives for themselves, but are still navigating all the surprises and unexpected turns that come with finding the right person,” Packer said. “This cast came in knowing who they are and what they want, but love has a way of challenging even our best-laid plans. That’s what makes this journey, and this season, fun to watch.”
This season also introduces a first for the franchise: a sibling duo embarking on the dating experience together. Their shared journey adds another dimension to the process as the participants navigate attraction, relationships, and the possibility of finding a lasting connection.
Throughout the season, Nephew Tommy encourages the singles to look beyond first impressions and consider whether their relationships have the potential to develop into something deeper. As connections evolve, viewers can expect difficult decisions, unexpected pairings, and moments that challenge the participants’ ideas about love.
Meet the Ready to Love: Chicago Cast
Season 12 features 20 Chicago-area singles from a range of professional backgrounds.
Ashley, 39 — Chemist and real estate broker
Brandi, 33 — Digital campaign specialist
Brittany, 33 — Mental health therapist
Bryana, 35 — Spirits market manager
Champ, 46 — Sports radio producer
David, 31 — Sports analyst and MMA fighter
Hubert, 38 — Account director
Indaca, 37 — Flight attendant
Jarrette, 35 — Project manager
Jasmine, 34 — Tech CEO
Jessica, 31 — Banker and basketball coach
Jonathan, 34 — Facilities manager
Jordan, 35 — Energy company co-owner
Keith, 46 — Director of human resources
Kiara, 36 — Realtor
Marcus, 44 — Songwriter and producer
Michael, 37 — Digital marketing director
Patrick, 38 — District foreman
Precious, 37 — Defense industry operations program manager
Yuri, 41 — Attorney
Produced for OWN by Will Packer Media and Lighthearted Entertainment, Ready to Love: Chicago expands the popular dating franchise into a new city, bringing Chicago’s culture and community into the spotlight while exploring how successful Black singles approach relationships in their 30s and 40s.
How to Watch Ready to Love: Chicago
Tune in to the 12th season at 8 p.m. ET/PT on OWN.
For more information about the series, visit OWN’s official website.
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