Claim OwnershipToby + Chilli's "Crazy First Dates"
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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!
588 Episodes
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Mary in Burke met his parents on the first date...and was left alone with them.See omnystudio.com/listener for privacy information.
Laura from Germantown and the Warf walk that turned into a barf walk.See omnystudio.com/listener for privacy information.
Gina from Odenton tells us about the time skinny dipping took a wild turn… let’s just say it ended in theft, not romance.See omnystudio.com/listener for privacy information.
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. 🦷⏰ See omnystudio.com/listener for privacy information.
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. 👀💥See omnystudio.com/listener for privacy information.
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.See omnystudio.com/listener for privacy information.
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 nightsSee omnystudio.com/listener for privacy information.
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 ☔💋.See omnystudio.com/listener for privacy information.
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?See omnystudio.com/listener for privacy information.
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.See omnystudio.com/listener for privacy information.
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!See omnystudio.com/listener for privacy information.
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?See omnystudio.com/listener for privacy information.
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.”See omnystudio.com/listener for privacy information.
Tony in Silver Spring shares how his night went from flirty to fleeing when a fight broke out mid-date 😳👊See omnystudio.com/listener for privacy information.
Rayna in Waldorf went on a date with a guy who made a huge stink about his medical condition.See omnystudio.com/listener for privacy information.
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? 🎬See omnystudio.com/listener for privacy information.
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!See omnystudio.com/listener for privacy information.
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!See omnystudio.com/listener for privacy information.
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.See omnystudio.com/listener for privacy information.
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.See omnystudio.com/listener for privacy information.
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