Toby + Chilli's "Crazy First Dates"

Tony in Silver Spring shares how his night went from flirty to fleeing when a fight broke out mid-date

Rayna in Waldorf went on a date with a guy who made a huge stink about his medical condition. 

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?

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!

Maria's in Crofton's date went south fast when he got sick in her car

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.

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.

Gina from Odenton thought a late-night skinny dip sounded romantic... until her date's clothes were stolen and things went downhill fast.

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"

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!

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!

Chrissy in Hagerstown went on a first date that got crazy when his ex walked up and stole him right back!

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!

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!

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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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!

Mike from Springfield—what happens on the booze cruise doesn't stay on the booze cruise!

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…

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!

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!

Things were going great for  Jen in Reston. She thought she was going on a normal first date… until things took a wild turn!

Heather from Stafford thought she was in for a great night… until there was a smell that made things awkward—FAST!

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?

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!

Bonnie from Gainesville went on a date... but things took a weird turn when her hippie suitor invited her into his van.

Elizabeth in DC's first date took an unexpected turn when her son decided he wasn't a fan—so he launched a toy at her date!

Lisa in Baltimore went on a first date that had an awkward kiss. She went to the bathroom to send her friends a snap about it and she sent it to the wrong person. Who got it and how did it change the date? Listen here to this Crazy First Date story to find out!

Tina in Falls Church went on a first date with a guy at Kings Dominion. He brought a friend he didn't tell her about, and she ended up liking the friend better. Did she end up on a second date with either of them? Listen to this Crazy First Date story to find out!

Kris in D.C. was at a nice restaurant when her date ordered extra lettuce for the pet turtle, he pulled out of a gift bag. How did she react? Find out with this Crazy First Date story!

Sean invited his first date on a trip to Dubai! Did she go on the trip or RUN?! Listen to this Crazy First Date Story to find out!

Dating can be an adventure, but for Devin from DC, her first date took a wild turn when a medical emergency turned things upside down

Adam in Falls Church did a little too much pre-gaming before his first date, and it ended in a manager needing keys to get him out! Listen to this Crazy First Date to hear what happened, and if there was a second date.

Cee Cee in King George was proposed to on the first date! Was that the end of the date or did she say yes? Listen to this Crazy First Date Story to find out!

Natalie in Bethesda met someone on Tinder and on minutes into their first date they had to sign a waiver because they were being featured on a reality tv show before the drinks even arrived! Listen to this Crazy First Date Story to find out if they're still together or if it was too weird to go on!

Melissa in Gainsville went on a first date and she had to tell a white lie that caught up to her. Did it end the date, or end in forever? Listen to this Crazy First Date Story to find out!

Kristie in Alexandria set someone up with her sister. Turns out he liked Kristie better. How did their first date go, and did it lead to forever? Listen to this Crazy First Date Story to find out!

Jamie in Wheaton finally got a first date with a co-worker she was crushing on. Except she lost her balance and tumbled down concrete stairs after their lunch date. Did he help her get some band aids or was the date done for good? Listen to this Crazy First Date to find out!

Lisa in Baltimore went on a Crazy First Date, and it wasn't going well. She decided to send her friends a snap and it accidentally sent it to the wrong person. Whoops! Find out who she sent it to and whether there was a second date.

Donna in Purceville went on a first date and before they could order dessert he was asking her to meet his family and join their family vacation… the next day! Listen to this Crazy First Date story to hear if she went on the trip.

Mike in Springfield went on a booze cruise for his first date and they ran into someone they didn't expect, that left everyone a little embarrassed. Listen to this Crazy First Date Story to find out who they ran into and if forever was in the cards.

Kevin in Rockville went on a Crazy First Date that started with sugar in his gas tank, and ended up with someone he didn't even recognize. Listen to find out how all of this happened on the first date.

Kim in D.C. went on a first date and got an earful about certain foods she ordered. What did he say, and why so mean? Listen to this Crazy First Date to find out how it ended.

Wendy in Hagerstown went on a first date that began with some very inappropriate questions that made her walk out. Listen here to find out what he asked and whether he tried to see her again.

Jeri in Rockville went on a first date that ended in a movie theater with a kiss that left her with a mustache. Find out how that even happens, and whether they saw each other again, with this Crazy First Date story!

Regina in D.C. went on a first date to a gentleman's club and ended the night going on a cross country road trip. Listen to this Crazy First Date to find out where they went and if they ever saw each other again.

Kris in D.C. met a guy for a first date at a restaurant and he brought his pet turtle and wanted her to order lettuce to feed it. Did she, and was there a second date? Listen to this Crazy First Date to find out!

Liz in D.C. was a single Mom whose date came to pick her up. Her son didn't like him and threw a toy car. There were injuries, but did they go through with the date? Listen to this Crazy First Date story to find out!

He had a great date planned until she broke out a costume in the middle of a restaurant. How did that go and did they ever see each other again? Listen to this Crazy First Date Story to find out!