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| Episode | Episode Name | Air Date | | 1 | Chicago Hopefuls | Tue Oct 15, 2024 | | 2 | Windy City Weddings | Tue Oct 22, 2024 | | 3 | Did Ya'll Meet My Husband? | Tue Oct 29, 2024 | | 4 | Wedding Bliss or a Miss | Tue Nov 12, 2024 | | 5 | A Beach of a Honeymoon | Tue Nov 19, 2024 | | 6 | Never Forget About Karla | Tue Nov 26, 2024 | | 7 | Basement Blues | Tue Dec 03, 2024 | | 8 | Chef's Kiss and a Rude Diss | Tue Dec 10, 2024 | | 9 | You Into Some Crazy Stuff? | Tue Dec 17, 2024 | | 10 | Anniversary Dinner Showdown | Tue Jan 07, 2025 | | 11 | She Said/He Fled | Tue Jan 14, 2025 | | 12 | I Just Wanna Eat You Up | Tue Jan 21, 2025 | | 13 | The Truth Always Come Out | Tue Jan 28, 2025 | | 14 | Lies, Lies, Lies! | Tue Feb 04, 2025 | | 15 | Cheat and Retreat | Tue Feb 11, 2025 | | 16 | The Experts Have Questions | Tue Feb 18, 2025 | | 17 | A Match Made in Scandal | Tue Feb 25, 2025 | | 18 | New Love is in the Air | Tue Mar 04, 2025 | | 19 | Chicago Reunion, Part 1 | Tue Mar 11, 2025 | | 20 | Chicago Reunion, Part 2 | Tue Mar 18, 2025 | | Special | Matchmaking in Chicago | Tue Oct 08, 2024 | | Special | Kicking Off Chicago | Tue Oct 08, 2024 | | Special | The Journey So Far: Chicago | Tue Jan 07, 2025 | | Special | Secrets Revealed Special | Tue Mar 11, 2025 | | Special | Where Are They Now: It's Vow or Never | Tue Mar 25, 2025 |
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