- Bryana and Jordan share genuine chemistry, bonding over shared faith values and what matters in a lasting partnership.
- The couple’s playful banter turns flirty when Bryana makes a spicy compliment about Jordan’s appearance during their date.
- Chicago’s first season introduces 20 successful Black singles in their 30s-40s, including the show’s first sibling duo seeking love.
Another episode of Ready To Love is bringing some seriously spicy flirting to the Windy City, and BOSSIP’s got your exclusive first look!

As previously reported, the Chicago season of OWN’s long-running dating series, which premiered Oct. 2, follows 20 successful Black singles in their 30s and 40s as they navigate the highs and lows of finding lasting love.
Hosted by Thomas “Nephew Tommy” Miles, the season marks the franchise’s first time filming in Chicago and features a diverse group of entrepreneurs, executives, attorneys, and creatives. It also introduces the show’s first sibling duo, who are searching for love side by side.
With plenty of personalities and potential pairings in the mix, the Chicago singles are discovering whether their connections can go beyond initial attraction.
Ready To Love Exclusive Clip
BOSSIP has an exclusive clip from Friday’s new episode featuring Bryana and Jordan on a pickleball date that starts with a sweet compliment and takes a flirtatious turn.

Jordan kicks things off by telling Bryana she smells good, which she admits is one of her favorite compliments.
And judging by her confessional, she’s already feeling the chemistry.
“I’m really excited about this date because, baby, I want to see Jordan,” says Bryana. “I have been having my eye on him. You know, he’s got it going on.”
She also candidly admits that she’s open to taking their attraction to another level.
“So do I want to bump uglies with Jordan? Possibly,” she says with a laugh.

Beyond the physical attraction, the two discuss what they’re looking for in a lasting relationship, including the importance of faith.
Jordan opens up about being a supportive partner in past relationships without always receiving the same commitment in return. He also explains that his faith guides the man he hopes to become.

“I know that God has put me on this earth to do something bigger than me,” he says.
Bryana appreciates his perspective, especially because her own faith is nonnegotiable.
“That is so important to me because I cannot waver on my faith,” she tells him. “And I want a partner that also leans on God to make decisions for us.”
The conversation takes another promising turn when Jordan asks Bryana how she feels about their connection.
“I see our connection as something that has authentic potential,” she says. “I have a warm, safe feeling when I talk to you.”
Jordan, however, wants to know what it would take to turn up the heat.
“What would it take to go from warm to hot?” he asks.
And that’s when things turn up.
“Well, first of all, you bald,” Bryana tells him. “I don’t mind the bald head. I’ll lick it.”

Bryana catches Jordan off guard, prompting him to describe the moment as “awkward” in his confessional, although he admits he’s also a little flattered.

Bryana then compares his bald head to the yellow M&M before making another flirty request.
“Take off your shirt,” she tells him.
Jordan jokes in his confessional that getting undressed might be the best way to get to know her, but ultimately, he seems pleased with their sporty date.
“After this date, I definitely feel a stronger connection with Bryana, just from our playful banter, the flirtiness,” he says. “And I would like to get to know her more deeply.”
Take an exclusive look at their date below!
What do YOU think about Bryana and Jordan’s connection? Do you see some potential?
