| 1 | 11/7 – Lisa in Baltimore and the Snap Chat Mistake 2024-11-07 |
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| 2 | 11/5 – Donna in Purceville & The First Date Flight Offer 2024-11-05 |
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| 3 | 10/31 – Mike in Springfield and the Booze Cruise 2024-10-31 |
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| 4 | 10/29 – Kevin in Rockville & The Sugar Gas Tank 2024-10-29 |
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| 5 | 10/24 – Kim in D.C. and the Controversial Food Order 2024-10-24 |
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| 6 | 10/21 – Wendy in Hagerstown & the Inappropriate Questions 2024-10-22 |
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| 7 | 10/17 – Jeri in Rockville and the Unexpected Mustache 2024-10-17 |
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| 8 | 10/15 – Regina and the Cross-Country Road Trip Date 2024-10-15 |
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| 9 | 10/10 – Kris in D.C. and the Restaurant Turtle 2024-10-10 |
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| 10 | 10/8 – Liz in D.C. and the Toy Car Incident 2024-10-08 |
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Toby + Chilli's "Crazy First Dates"
Have you ever had a Crazy First Date story that's SO good it needs to be shared with the WORLD?! Remember, doesn’t have to be your worst… just your first!
