*“Ready to Love” is packing up its dating experiment and heading to Chicago for the first time, bringing a new group of Black singles together to see whether sparks can survive beyond that promising first date.
“Ready to Love: Chicago” premieres Friday, Oct. 2 on OWN, with Thomas “Nephew Tommy” Miles returning as host. According to the news release, the new season follows successful singles in their 30s and 40s looking for serious relationships — and trying to figure out who’s genuinely ready for one.
Chicago becomes the latest city to host the long-running dating franchise after previous seasons took the search for love to Atlanta, Houston, Miami, Fort Worth and Detroit.
Chicago Singles Enter the Dating Pool
The new cast includes entrepreneurs, executives, attorneys, creatives and community leaders, but professional success won’t necessarily make navigating romance any easier.
Miles will challenge the singles to move beyond physical attraction and first impressions as they explore compatibility, communication, family expectations, personal values, and what they actually want from a future partner.
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That’s familiar territory for the host. During EURweb’s exclusive conversation about “Ready to Love: Detroit”, Miles explained why he pushes participants to become more emotionally available during the process.
“I think it’s my job to make sure, first of all, you’re vulnerable, that you want to open up and show what you haven’t shown in the past,” he told EURweb.
He also pointed out the obvious dilemma facing contestants who arrive with established lives but haven’t found the relationship they want: “Whatever you’ve been doing hasn’t been working.”
Now he’ll be delivering that reality check Chicago-style.
Two Siblings Search for Love Together
The Chicago season also introduces something the franchise hasn’t tried before: a sibling duo entering the experience together.
Having a sibling nearby could provide an unusually informed second opinion when romantic red flags start waving. It could also make things awkward if one sibling’s dating choices don’t exactly impress the other.
Beyond that twist, the show’s central question remains unchanged: Can a group of accomplished adults put aside old patterns, become vulnerable and make a connection capable of lasting after the cameras stop rolling?
“Ready to Love” has been asking variations of that question for years. EURweb has followed the franchise since its early Atlanta days and has repeatedly spoken with Nephew Tommy about his role guiding singles through the process.
This time, Chicago gets to answer.
Tune in to “Ready to Love: Chicago” Friday, Oct. 2 at 8 p.m. ET/PT. Watch the trailer above.
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