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

Tina from Falls Church and the Unexpected +1

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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Janet in Annandale and the Solo Dinner Date

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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Bria in D.C. and the Guy from the Gym

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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Lydia in Bel Air and the made for TV moment

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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Shaun in Fairfax and the Dubai Date

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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Natalie in Falls Church and the Taylor Swift Liar

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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Bonnie from Gainesville and the Creepy Artist

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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Darby in Gaithersburg & The Bowling Date Blunder

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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Emily in Reston and The Purity Police

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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Tony in Silver Spring and the Bar Fight

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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Rayna in Waldorf and the Stinky Date

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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Anja in Silver Spring and the Vanishing Act

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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Caroline in D.C. and the Over Planner

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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Maria in Crofton and the guy who swooped in to help

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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Karen in Fredericksburg and the First Date Flight

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 in Alexandria and the Dating Contract

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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Gina in Odenton and the Skinny-Dipping Clothes Stealer!

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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Trinidad in Arlington and the Lost Name

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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Michelle in Bethesda and the Leftovers and Letdowns

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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Donna in Nokesville and the Free Date

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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