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
May 29, 2025 • 1 min
Creepy! Bonnie from Gainesville had a first date with an artist who wanted her to check out his art in his van! He's creepy. Crude. Made one artistic first impression!
Mark as Played
May 27, 2025 • 2 mins
Darby in Gaithersburg called in with a dating story that had us cringing and cracking up! Imagine showing up for a fun night of bowling... only to realize someone forgot to bring money. 😬 Was it a simple mistake or a sneaky test?
Mark as Played
May 20, 2025 • 2 mins
Emily in Reston thought she met a sweet guy from her church’s childcare center. Harmless, right? Nope. One dinner in, and he storms out—offended that a single mom doesn’t meet his “purity standards.”
Mark as Played
May 15, 2025 • 2 mins
Tony in Silver Spring shares how his night went from flirty to fleeing when a fight broke out mid-date 😳👊
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May 13, 2025 • 2 mins
Rayna in Waldorf went on a date with a guy who made a huge stink about his medical condition.
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May 8, 2025 • 2 mins
Anya from Silver Spring thought she was in for a low-key first date at the movies—until her date disappeared halfway through the film. No goodbye. No text. Just gone. When he finally reached out, the excuse he gave was so bizarre, we had to hear it twice. Was it legit… or the most creative ghosting ever? 🎬
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May 6, 2025 • 2 mins
Caroline from DC shares how her sweet (but seriously over-prepared) date packed way too much into one day—from brunch to a museum to a scenic hike and beyond. She was exhausted, he missed all the hints. Listen to find out if there was a second date!
Mark as Played
May 1, 2025 • 2 mins
Maria’s in Crofton’s date went south fast when he got sick in her car 🤮 but wait till you hear who came to the rescue!
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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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April 24, 2025 • 2 mins
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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April 22, 2025 • 2 mins
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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April 18, 2025 • 2 mins
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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April 10, 2025 • 2 mins
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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April 8, 2025 • 2 mins
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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April 3, 2025 • 3 mins
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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April 1, 2025 • 2 mins
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March 27, 2025 • 2 mins
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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March 25, 2025 • 2 mins
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.
Mark as Played
March 18, 2025 • 2 mins
"🚨🚩 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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