Episode 1
Don't Be Shy in the Chi
Oct 2, 2026
RTL blows into the Windy City for a speakeasy mixer featuring 20 of Chicago's finest singles. While several romances form, six of the singles fail to make a good first impression in the Second City and find themselves facing elimination the first night.
Episode 2
Second Chances in the Second City
Oct 9, 2026
The men have the power as the ladies have their first chance to make a second impression.
Episode 3
Stepping Into Your Chicago
Oct 16, 2026
The women are in power this week, and Tommy encourages them to invite the men into their world.
Episode 4
Exes and Ohs
Oct 23, 2026
Tommy drops a bomb by bringing the singles' exes to a high-stakes mixer.
Episode 5
Curious About the Pickle
Oct 30, 2026
The singles get deeper by discussing their fears with one another.
Episode 6
Dealbreakers
Nov 6, 2026
With the women in power, Tommy assigns them the task of examining dealbreakers with their connections.
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