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
July 29, 2025 • 2 mins
Mary in Burke met his parents on the first date...and was left alone with them.
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July 24, 2025 • 2 mins
Laura from Germantown and the Warf walk that turned into a barf walk.
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July 17, 2025 • 2 mins
Gina from Odenton tells us about the time skinny dipping took a wild turn… let’s just say it ended in theft, not romance.
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July 15, 2025 • 2 mins
Marco showed up late, then ended the date early for a dentist appointment?! Let’s just say, this Germantown guy left more questions than sparks. 🦷⏰
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July 1, 2025 • 1 min
Tina thought she was meeting one guy for a first date… but he brought a plus one. 😬 What happened next? Let’s just say sparks flew… but not where you'd expect. 👀💥
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June 24, 2025 • 2 mins
Janet from Annandale thought she was in for a nice night out... until her date left in the middle of dinner to run errands. Yep, she was literally left sitting at the table. Alone.
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June 19, 2025 • 2 mins
Bria from D.C., decided to take a chance on the very intense guy from his gym—you know, the one who stares too long between reps 😳. What started with protein shakes and awkward small talk quickly spiraled into one of the most bizarre nights
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June 17, 2025 • 1 min
Lydia from Bel Air, MD shares a first date that could’ve been ripped straight from a rom-com script 🎬. It started with nerves, took a turn with a downpour, and ended in the kind of rain-soaked moment you only see in movies. Was it love, chaos, or both? Tune in to hear how Lydia’s unforgettable date went from ordinary to Hollywood-worthy—umbrellas not included ☔💋.
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June 5, 2025 • 1 min
Shaun in Fairfax was stationed in Dubai when he invited someone special—someone he'd only talked to online—to fly from the U.S. and meet him. Romantic? Risky? Both? She said yes... but how did this long-distance leap of faith play out? Was it a fairy tale ending—or a total disaster?
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June 3, 2025 • 2 mins
It started with Taylor Swift and ended with... a very unexpected body fact. 😳 One lie, one awkward moment, and a whole lot of secondhand cringe.
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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!
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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?
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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.”
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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!
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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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