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

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?
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.
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! 
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?
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.”
Mark as Played
Tony in Silver Spring shares how his night went from flirty to fleeing when a fight broke out mid-date 😳👊
Mark as Played
Rayna in Waldorf went on a date with a guy who made a huge stink about his medical condition. 
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? 🎬
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!
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!
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.
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.
Mark as Played
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.
Mark as Played
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"
Mark as Played
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!
Mark as Played
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!
Mark as Played
Chrissy in Hagerstown went on a first date that got crazy when his ex walked up and stole him right back!
Mark as Played
Adam from Bethesda shares his unforgettable night at a seafood restaurant where his date turned the evening into an unexpected performance—complete with costumes and spontaneous dancing. Was it a quirky red flag or just a seafood-fueled good time? Tap to hear all the wild details!
Mark as Played
Lane in Hughesville judged a book by its cover and then ended up with a husband. Find out how a bad first date turned into marriage!
Mark as Played

Popular Podcasts

    The latest news in 4 minutes updated every hour, every day.

    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.

    Crime Junkie

    Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

    The Clay Travis and Buck Sexton Show

    The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

    True Crime Tonight

    If you eat, sleep, and breathe true crime, TRUE CRIME TONIGHT is serving up your nightly fix. Five nights a week, KT STUDIOS & iHEART RADIO invite listeners to pull up a seat for an unfiltered look at the biggest cases making headlines, celebrity scandals, and the trials everyone is watching. With a mix of expert analysis, hot takes, and listener call-ins, TRUE CRIME TONIGHT goes beyond the headlines to uncover the twists, turns, and unanswered questions that keep us all obsessed—because, at TRUE CRIME TONIGHT, there’s a seat for everyone. Whether breaking down crime scene forensics, scrutinizing serial killers, or debating the most binge-worthy true crime docs, True Crime Tonight is the fresh, fast-paced, and slightly addictive home for true crime lovers.

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

Connect

© 2025 iHeartMedia, Inc.