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

July 29, 2025 1 min
Mary in Burke met his parents on the first date...and was left alone with them.

See omnystudio.com/listener for privacy information.

Mark as Played
Laura from Germantown and the Warf walk that turned into a barf walk.

See omnystudio.com/listener for privacy information.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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

See omnystudio.com/listener for privacy information.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played
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.

Mark as Played

Popular Podcasts

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Ruthie's Table 4

    For more than 30 years The River Cafe in London, has been the home-from-home of artists, architects, designers, actors, collectors, writers, activists, and politicians. Michael Caine, Glenn Close, JJ Abrams, Steve McQueen, Victoria and David Beckham, and Lily Allen, are just some of the people who love to call The River Cafe home. On River Cafe Table 4, Rogers sits down with her customers—who have become friends—to talk about food memories. Table 4 explores how food impacts every aspect of our lives. “Foods is politics, food is cultural, food is how you express love, food is about your heritage, it defines who you and who you want to be,” says Rogers. Each week, Rogers invites her guest to reminisce about family suppers and first dates, what they cook, how they eat when performing, the restaurants they choose, and what food they seek when they need comfort. And to punctuate each episode of Table 4, guests such as Ralph Fiennes, Emily Blunt, and Alfonso Cuarón, read their favourite recipe from one of the best-selling River Cafe cookbooks. Table 4 itself, is situated near The River Cafe’s open kitchen, close to the bright pink wood-fired oven and next to the glossy yellow pass, where Ruthie oversees the restaurant. You are invited to take a seat at this intimate table and join the conversation. For more information, recipes, and ingredients, go to https://shoptherivercafe.co.uk/ Web: https://rivercafe.co.uk/ Instagram: www.instagram.com/therivercafelondon/ Facebook: https://en-gb.facebook.com/therivercafelondon/ For more podcasts from iHeartRadio, visit the iheartradio app, apple podcasts, or wherever you listen to your favorite shows. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.