‘Ready To Love: Chicago’ Cast: Meet The Windy City Singles Seeking Love, Including THIS Familiar Face

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.

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