Toby + Chilli's "Crazy First Dates"

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

April 29, 2025 2 mins
Karen in Fredericksburg flew to another state for a first date... but the story took a wild turn she never saw coming ✈️❤️. Let’s just say she didn’t come home alone.
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Katie thought she was heading out for a normal night—dinner, conversation, maybe a spark. But her date had other plans... including a contract and a wildly unexpected comment about her body.
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Gina from Odenton thought a late-night skinny dip sounded romantic... until her date’s clothes were stolen and things went downhill fast. 😳💦 Would YOU stick around or run for cover? This one’s unforgettable.
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Trinidad in Arlington went on a first date with someone also named after a famous boxer. What a cooincidence! She still forgot his name though and it got weird. Listen to this Crazy First Date story to hear if it ended in love or he said "see ya"
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She got set up by her boss and it go weird when he said he was relieved she wasn’t a “leftover”. Listen to this Crazy First Date to find out if it ended in love a or quick exit!
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Donna from Nokesville shares her unforgettable first date experience where he got the entire date comped. Was it a deal breaker or love at first sight? Listen to this Crazy First Date story to find out!
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Chrissy in Hagerstown went on a first date that got crazy when his ex walked up and stole him right back!
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Adam from Bethesda shares his unforgettable night at a seafood restaurant where his date turned the evening into an unexpected performance—complete with costumes and spontaneous dancing. Was it a quirky red flag or just a seafood-fueled good time? Tap to hear all the wild details!
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Lane in Hughesville judged a book by its cover and then ended up with a husband. Find out how a bad first date turned into marriage!
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March 20, 2025 2 mins
Leslie in Herndon thought she had a perfectly decent first date—until they parted ways and he found himself in jail. Why was he arrested and did Leslie come to bail him out? Find out if there was ever a second date after this disastrous detour.
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"🚨🚩 When a gym crush turns into a full-blown cyber detective! This week on Crazy First Dates, she thought she was meeting a nice guy from her gym—until he started deep-diving into her ex-husband’s online life. 🚨 Stalker vibes? You decide. Listen now! 
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Lydia's first date started with a simple walk—but Mother Nature had other plans. When the skies opened, the night took an unexpected turn. Did the downpour wash away the spark, or was it the start of something unforgettable? Listen in to find out! 💕 #CrazyFirstDates #LoveInTheRain #RadioRomance
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Mike from Springfield—what happens on the booze cruise doesn’t stay on the booze cruise! 🚢🍾😳 Hear how a wedding weekend took an unexpected turn! #CrazyFirstDates #BoozeCruiseConfessions
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Lindsey in Arlington thought it was just a simple dinner date with a guy from college—until his ex showed up at the restaurant. What happened next? Let’s just say he didn’t stick around for dessert… 😳🍽️
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February 27, 2025 1 min
Jamie in Wheaton had a first date to remember—for all the wrong reasons. She managed to fall down a flight of concrete stairs not once, but twice! Did her date stick around, or was this a romance doomed from the first tumble? Tune in to find out!
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Janet in Annandale thought her date was going well—until he suddenly left to run errands in the middle of it. Was he multitasking his way into her heart, or was this just a bizarre brush-off? Listen to hear how it all went down and whether this odd detour led to a second date or a dead end!
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February 20, 2025 2 mins
Things were going great for  Jen in Reston. She thought she was going on a normal first date… until things took a wild turn! 😳💍 Instead of romance, she got a polygamy invitation! 😱 You must hear this one. 🎧🔥 #CrazyFirstDates #DatingFails #WaitWHAT
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Heather from Stafford thought she was in for a great night… until there was a smell that made things awkward—FAST! 💨😳 Would you stick it out or run for fresh air? 😂 Tune in for the hilarious (and slightly smelly) details! #CrazyFirstDates #DatingDisasters #HoldYourBreath
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February 13, 2025 2 mins
Amalie in Vienna thought she was in for a romantic boat date—but instead, she found herself on a barely-floating disaster. When her date insisted, they set sail anyway, things went from bad to completely unseaworthy. Would you have stayed on board?
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