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

Katie in Alexandria and the Dating Contract

April 24, 2025 • 2 mins
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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Gina in Odenton and the Skinny-Dipping Clothes Stealer!

April 22, 2025 • 2 mins
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.
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Trinidad in Arlington and the Lost Name

April 18, 2025 • 2 mins
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"
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Michelle in Bethesda and the Leftovers and Letdowns

April 10, 2025 • 2 mins
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!
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Donna in Nokesville and the Free Date

April 8, 2025 • 2 mins
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!
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Chrissy in Hagerstown Had Her Date Stolen—Right in Front of Her!"

April 3, 2025 • 3 mins
Chrissy in Hagerstown went on a first date that got crazy when his ex walked up and stole him right back!
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Tita in Woodbridge and the one time with a catfish she met on the Facebook Dating App!

April 1, 2025 • 2 mins
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Adam in Bethesda and the Seafood Spectacle

March 27, 2025 • 2 mins
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!
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Lane in Hughesville and the “Geek”

March 25, 2025 • 2 mins
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!
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Leslie in Herndon and the Jail Call

March 20, 2025 • 2 mins
Leslie in Herndon thought she had a perfectly decent first date—until they parted ways and he found himself in jail. Why was he arrested and did Leslie come to bail him out? Find out if there was ever a second date after this disastrous detour.
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Bria in D.C. and the Ex-Husband Deep Dive

March 18, 2025 • 2 mins
"🚨🚩 When a gym crush turns into a full-blown cyber detective! This week on Crazy First Dates, she thought she was meeting a nice guy from her gym—until he started deep-diving into her ex-husband’s online life. 🚨 Stalker vibes? You decide. Listen now! 
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Lydia in Bel Air and the Rainy Romance 🌧️

March 11, 2025 • 1 min
Lydia's first date started with a simple walk—but Mother Nature had other plans. When the skies opened, the night took an unexpected turn. Did the downpour wash away the spark, or was it the start of something unforgettable? Listen in to find out! 💕 #CrazyFirstDates #LoveInTheRain #RadioRomance
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Mike From Springfield Busted on the Booze Cruise

March 6, 2025 • 1 min
Mike from Springfield—what happens on the booze cruise doesn’t stay on the booze cruise! 🚢🍾😳 Hear how a wedding weekend took an unexpected turn! #CrazyFirstDates #BoozeCruiseConfessions
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Lindsey in Arlington and the in-Person Ghosting

March 4, 2025 • 1 min
Lindsey in Arlington thought it was just a simple dinner date with a guy from college—until his ex showed up at the restaurant. What happened next? Let’s just say he didn’t stick around for dessert… 😳🍽️
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Jamie in Wheaton Tumbling into Love

February 27, 2025 • 1 min
Jamie in Wheaton had a first date to remember—for all the wrong reasons. She managed to fall down a flight of concrete stairs not once, but twice! Did her date stick around, or was this a romance doomed from the first tumble? Tune in to find out!
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Janet in Annandale and Errands Over Romance

February 25, 2025 • 2 mins
Janet in Annandale thought her date was going well—until he suddenly left to run errands in the middle of it. Was he multitasking his way into her heart, or was this just a bizarre brush-off? Listen to hear how it all went down and whether this odd detour led to a second date or a dead end!
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Jen in Reston & The Polygamy Invitation

February 20, 2025 • 2 mins
Things were going great for  Jen in Reston. She thought she was going on a normal first date… until things took a wild turn! 😳💍 Instead of romance, she got a polygamy invitation! 😱 You must hear this one. 🎧🔥 #CrazyFirstDates #DatingFails #WaitWHAT
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Heather in Stafford and the Date That Truly Stunk! 🤢💨

February 18, 2025 • 1 min
Heather from Stafford thought she was in for a great night… until there was a smell that made things awkward—FAST! 💨😳 Would you stick it out or run for fresh air? 😂 Tune in for the hilarious (and slightly smelly) details! #CrazyFirstDates #DatingDisasters #HoldYourBreath
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Amalie in Vienna and the Sinking Boat

February 13, 2025 • 2 mins
Amalie in Vienna thought she was in for a romantic boat date—but instead, she found herself on a barely-floating disaster. When her date insisted, they set sail anyway, things went from bad to completely unseaworthy. Would you have stayed on board?
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Maureen in Manassas and the Creepy Backroads

February 11, 2025 • 1 min
Maureen in Manassas went on a first date that started out ok, then it almost ended in a true crime episode. Listen to this Crazy First Date story to find out what happened!
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