Toby + Chilli's "Crazy First Dates"

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 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 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 shares how his night went from flirty to fleeing when a fight broke out mid-date 😳👊

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Rayna in Waldorf went on a date with a guy who made a huge stink about his medical condition.

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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 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’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 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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