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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.

The men have the power as the ladies have their first chance to make a second impression. Sleeves delves into sexual scripture. Marcus washes Ashley's feet. The Secret Siblings are revealed. Michael uses a fork on his pizza! Please, sir! This isn't steak!

The women are in power this week, and Tommy encourages them to invite the men into their world. Between roller skating, wine tasting, and game shows, the ladies dig deeper and learn new qualities from the guys while showing them their own side of Chicago.

Tommy drops a bomb by bringing the singles' exes to a high-stakes mixer. Jealousy and confessions are unleashed, and one person becomes history.

The singles get deeper by discussing their fears with one another. Michael and Precious ride off into the sunset. Bryana surprises Jonathan with her vulnerability. After learning new information, Jordan must make a tough decision about a connection.