Ready To Love is bringing the dating drama to the Windy City and including a familiar face for watchers of another dating franchise.
OWN’s long-running dating series is switching up the scenery for Ready To Love: Chicago, premiering Friday, Oct.2 at 8 p.m. ET. Hosted by Thomas “Nephew Tommy” Miles, the new season follows successful Black singles in their 30s and 40s as they date, flirt, and figure out whether they are actually ready for a lasting relationship.
According to OWN’s press release, this season features a variety of singles — from entrepreneurs and executives to attorneys and creatives. It also introduces the franchise’s first sibling duo, who will be searching for love side by side.
But one contestant already has reality TV history. Jarette, 35, is a Project Manager who previously appeared on Netflix’s Love Is Blind Season 2.
Jarette married Iyanna McNeely after their time in the pods, but the couple eventually divorced. Netflix’s Tudum confirms that their relationship ended after lifestyle differences became a major source of tension.
In 2023, we reported that the two traded cheating allegations, with Iyanna alleging that Jarrette kissed and groped a woman in their marital bed, while Jarrette alleged that he’d seen his wife holding hands with another man. Now viewers can see what dating has been like post-divorce for the Chicagoan.
The Chicago season of Ready To Love marks the first time the franchise has filmed in the city. With a reality TV veteran in the cast, a sibling duo, and 20 singles looking for love, OWN might have another messy season on its hands.
Ready To Love: Chicago premieres Friday, October 2 at 8 p.m. ET/PT on OWN.
Now, let’s meet the rest of the Chicago crew as reported by ESSENCE.
Meet The Singles
Ashley, 39, Real Estate Broker
Ashley works in real estate and is stepping into the dating experiment, hoping to find a connection that can go beyond the usual Chicago dating scene.
Brandi, 33, Digital Campaign Specialist
Brandi works in digital campaigns and joins the cast ready to see whether she can turn professional networking skills into a personal connection.
Brittany, 33, Mental Health Therapist
As a mental health therapist, Brittany knows communication matters. Now she gets to put those relationship skills to the test in her own love life.
Bryanna, 35, Spirits Market Manager
Bryanna works in the spirits industry and is bringing her professional confidence into the search for someone who can match her energy.
Champ, 46, Sports Radio Producer
Champ works behind the scenes in sports radio and is one of the more seasoned singles looking for a relationship with real staying power.
David, 31, Sports Analyst and MMA Fighter
David balances sports analysis with life as an MMA fighter, giving him a competitive edge that could make dating interesting.
Hubert, 38, Account Director
Hubert works as an account director and is hoping his career success translates into success in the dating department.
Indaca, 37, Flight Attendant
Indaca’s career keeps her traveling, so finding someone who can connect with her lifestyle could be part of the challenge.
Jarette, 35, Project Manager
Yes, that Jarette. After Love Is Blind, he is giving reality TV romance another shot.
Jasmine, 34, Tech CEO
Jasmine is a business leader who is used to calling the shots. Now she has to figure out who can meet her at her level emotionally.
Jessica, 31, Banker and Basketball Coach
Jessica balances finance with coaching, giving her a career that requires both discipline and people skills.
Jonathan, 34, Facilities Manager
Jonathan works in facilities management and enters the experiment hoping to find someone who fits into the bigger picture of his life.
Jordan, 35, Energy Company Co-Owner
Jordan is an entrepreneur in the energy industry who is looking for a partner to build something meaningful with.
Keith, 46, Senior Director of Human Resources
Keith works in HR, so he is no stranger to navigating people and personalities. Now he is searching for the right person for himself.
Kiara, 36, Realtor
Kiara works in real estate and joins a cast full of ambitious professionals looking for more than a casual connection.
Marcus, 44, Songwriter and Grammy-nominated Producer
Marcus brings music industry experience to the dating pool and could have a few smooth moves ready for the right woman.
Michael, 37, Digital Marketing Director
Michael works in digital marketing and understands how to make an impression. The question is whether he can make one that lasts.
Patrick, 38, District Foreman
Patrick works in a leadership role and is looking for someone who appreciates his work ethic and can meet him where he is.
Precious, 37, Chemical Engineer and Operations Leader
Precious brings brains, ambition and leadership experience to the cast while searching for a relationship that matches her drive.
