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!
Episodes
December 3, 2024 • 2 mins
Cee Cee in King George was proposed to on the first date! Was that the end of the date or did she say yes? Listen to this Crazy First Date Story to find out!
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November 21, 2024 • 2 mins
Natalie in Bethesda met someone on Tinder and on minutes into their first date they had to sign a waiver because they were being featured on a reality tv show before the drinks even arrived! Listen to this Crazy First Date Story to find out if they’re still together or if it was too weird to go on!
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November 19, 2024 • 2 mins
Melissa in Gainsville went on a first date and she had to tell a white lie that caught up to her. Did it end the date, or end in forever? Listen to this Crazy First Date Story to find out!
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November 14, 2024 • 2 mins
Kristie in Alexandria set someone up with her sister. Turns out he liked Kristie better. How did their first date go, and did it lead to forever? Listen to this Crazy First Date Story to find out!
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November 12, 2024 • 2 mins
Jamie in Wheaton finally got a first date with a co-worker she was crushing on. Except she lost her balance and tumbled down concrete stairs after their lunch date. Did he help her get some band aids or was the date done for good? Listen to this Crazy First Date to find out!
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November 7, 2024 • 2 mins
Lisa in Baltimore went on a Crazy First Date, and it wasn’t going well. She decided to send her friends a snap and it accidentally sent it to the wrong person. Whoops! Find out who she sent it to and whether there was a second date.
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November 5, 2024 • 1 min
Donna in Purceville went on a first date and before they could order dessert he was asking her to meet his family and join their family vacation… the next day! Listen to this Crazy First Date story to hear if she went on the trip.
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October 31, 2024 • 2 mins
Mike in Springfield went on a booze cruise for his first date and they ran into someone they didn’t expect, that left everyone a little embarrassed. Listen to this Crazy First Date Story to find out who they ran into and if forever was in the cards.
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October 29, 2024 • 2 mins
Kevin in Rockville went on a Crazy First Date that started with sugar in his gas tank, and ended up with someone he didn’t even recognize. Listen to find out how all of this happened on the first date.
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October 24, 2024 • 2 mins
Kim in D.C. went on a first date and got an earful about certain foods she ordered. What did he say, and why so mean? Listen to this Crazy First Date to find out how it ended.
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October 22, 2024 • 2 mins
Wendy in Hagerstown went on a first date that began with some very inappropriate questions that made her walk out. Listen here to find out what he asked and whether he tried to see her again.
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October 17, 2024 • 2 mins
Jeri in Rockville went on a first date that ended in a movie theater with a kiss that left her with a mustache. Find out how that even happens, and whether they saw each other again, with this Crazy First Date story!
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October 15, 2024 • 2 mins
Regina in D.C. went on a first date to a gentleman’s club and ended the night going on a cross country road trip. Listen to this Crazy First Date to find out where they went and if they ever saw each other again.
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October 10, 2024 • 2 mins
Kris in D.C. met a guy for a first date at a restaurant and he brought his pet turtle and wanted her to order lettuce to feed it. Did she, and was there a second date? Listen to this Crazy First Date to find out!
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October 8, 2024 • 2 mins
Liz in D.C. was a single Mom whose date came to pick her up. Her son didn’t like him and threw a toy car. There were injuries, but did they go through with the date? Listen to this Crazy First Date story to find out!
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October 3, 2024 • 1 min
He had a great date planned until she broke out a costume in the middle of a restaurant. How did that go and did they ever see each other again? Listen to this Crazy First Date Story to find out!
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October 1, 2024 • 1 min
Jennifer in Oakton went on a first date that got awkward when she had a coat wardrove malfunction. Listen here for find out how she got out of it, and whether she ever went out with him again.
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September 26, 2024 • 2 mins
Lilly in Annapolis couldn’t find his house, but when she finally did he had no furniture and tons of birds in cages. Did she even go on the date and did they see each other again? Listen here to this Crazy First Date to find out!
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September 24, 2024 • 2 mins
Kelly in Annapolis went on a Crazy First Date that started ok, then a chicken sandwich got involved and then it took a turn. Find out what happened, did they see each other again, and what happened to the chicken sandwich? Listen here to find out!
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September 19, 2024 • 2 mins
Wendy in Fairfax went on a first date where he took her to a jewelry store to pick our an engagement ring, except it wasn’t for her. Listen to this Crazy First Date story to find out who it was for, and how this Crazy First Date ended.
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