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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!... more
FAQs about Toby + Chilli's "Crazy First Dates":How many episodes does Toby + Chilli's "Crazy First Dates" have?The podcast currently has 588 episodes available.
July 29, 2025Mary in Buke and the Parent Tag-alongMary in Burke met his parents on the first date...and was left alone with them....more2minPlay
July 24, 2025Laura from Germantown and the Warf Walk that Turned into a Barf WalkLaura from Germantown and the Warf walk that turned into a barf walk....more3minPlay
July 17, 2025Gina in Odenton and the Skinny Dipping StealerGina from Odenton tells us about the time skinny dipping took a wild turn… let’s just say it ended in theft, not romance....more3minPlay
July 15, 2025Marco from Germantown and the Dentist AppointmentMarco showed up late, then ended the date early for a dentist appointment?! Let’s just say, this Germantown guy left more questions than sparks. 🦷⏰ ...more3minPlay
July 01, 2025Tina from Falls Church and the Unexpected +1Tina 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. 👀💥...more2minPlay
June 24, 2025Janet in Annandale and the Solo Dinner DateJanet 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....more3minPlay
June 19, 2025Bria in D.C. and the Guy from the GymBria 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...more3minPlay
June 17, 2025Lydia in Bel Air and the made for TV momentLydia 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 ☔💋....more2minPlay
June 05, 2025Shaun in Fairfax and the Dubai DateShaun 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?...more2minPlay
June 03, 2025Natalie in Falls Church and the Taylor Swift LiarIt started with Taylor Swift and ended with... a very unexpected body fact. 😳 One lie, one awkward moment, and a whole lot of secondhand cringe....more3minPlay
FAQs about Toby + Chilli's "Crazy First Dates":How many episodes does Toby + Chilli's "Crazy First Dates" have?The podcast currently has 588 episodes available.