Toby + Chilli's "Crazy First Dates"
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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!
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Mary in Buke and the Parent Tag-along
Mary in Burke met his parents on the first date...and was left alone with them.
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Laura from Germantown and the Warf Walk that Turned into a Barf Walk
Laura from Germantown and the Warf walk that turned into a barf walk.
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Gina in Odenton and the Skinny Dipping Stealer
Gina from Odenton tells us about the time skinny dipping took a wild turn… let’s just say it ended in theft, not romance.
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Marco from Germantown and the Dentist Appointment
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Tina from Falls Church and the Unexpected +1
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...
Janet in Annandale and the Solo Dinner Date
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 lef...
Bria in D.C. and the Guy from the Gym
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...
Lydia in Bel Air and the made for TV moment
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 dow...
Shaun in Fairfax and the Dubai Date
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...
Natalie in Falls Church and the Taylor Swift Liar
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.
Bonnie from Gainesville and the Creepy Artist
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...
Darby in Gaithersburg & The Bowling Date Blunder
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 rea...
Emily in Reston and The Purity Police
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...
Tony in Silver Spring and the Bar Fight
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 and the Stinky Date
Rayna in Waldorf went on a date with a guy who made a huge stink about his medical condition.
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Anja in Silver Spring and the Vanishing Act
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...
Caroline in D.C. and the Over Planner
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...
Maria in Crofton and the guy who swooped in to help
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 and the First Date Flight
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...
Katie in Alexandria and the Dating Contract
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 w...
Gina in Odenton and the Skinny-Dipping Clothes Stealer!
Gina from Odenton thought a late-night skinny dip sounded romantic... until her date’s clothes were stolen and things went downhill fast. 😳💦 Would Y...
Trinidad in Arlington and the Lost Name
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...
Michelle in Bethesda and the Leftovers and Letdowns
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 end...
Donna in Nokesville and the Free Date
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...
Chrissy in Hagerstown Had Her Date Stolen—Right in Front of Her!"
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!
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Adam in Bethesda and the Seafood Spectacle
Adam from Bethesda shares his unforgettable night at a seafood restaurant where his date turned the evening into an unexpected performance—complete wi...
Lane in Hughesville and the “Geek”
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
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 Lesli...
Bria in D.C. and the Ex-Husband Deep Dive
"🚨🚩 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—un...
Lydia in Bel Air and the Rainy Romance 🌧️
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 dow...
Mike From Springfield Busted on the Booze Cruise
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Lindsey in Arlington and the in-Person Ghosting
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? Le...
Jamie in Wheaton Tumbling into Love
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...
Janet in Annandale and Errands Over Romance
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 hea...
Jen in Reston & The Polygamy Invitation
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Heather in Stafford and the Date That Truly Stunk! 🤢💨
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...
Amalie in Vienna and the Sinking Boat
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, the...
Maureen in Manassas and the Creepy Backroads
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 f...
Bonnie in Gainsville and the First Date Creepy Van
Bonnie from Gainesville went on a date... but things took a weird turn when her hippie suitor invited her into his van. 🚐😳 Did she go inside, or was...