Have you ever been on a first date where you genuinely couldn't tell if the other person was messing with you?! Colin says his date with Paige was amazing... except for one VERY unusual thing she brought along. The more uncomfortable he got, the further Paige took the joke.See omnystudio.com/listener for privacy information.

What's hiding in your wallet right now? Because apparently that can make or break a first date. Joel and Simone were having an amazing night until she noticed something while he was paying. His reasoning makes perfect sense to HIM... but Simone started wondering if there was more to the story.See omnystudio.com/listener for privacy information.

The date was great. The chemistry was there. Adam even picked up the entire check. Green flags everywhere, right?! Well... Serafina happened to glance at the receipt before they left, and what she saw gave her an IMMEDIATE ick.See omnystudio.com/listener for privacy information.

Kevin went into this call thinking maybe he was just a little too nervous on his first date with Amanda. By the end, we're questioning how accurately he remembers the date AT ALL. Amanda has receipts, Kevin has excuses, and one tiny moment at the dinner table might be the ultimate first-date violation.See omnystudio.com/listener for privacy information.

Brian's first date with Sofia came with a surprise cast of characters he was NOT prepared for. What started as a great dinner quickly turned into a series of interactions that Sofia thought were hilarious... and Brian found slightly TERRIFYING. The biggest problem? He genuinely couldn't tell who was joking.See omnystudio.com/listener for privacy information.

Derek says the date with Vanessa had everything going for it… good convo, easy vibe, real attraction. The only curveball? She ended the night early and hasn’t said a word since. Did he misread the entire situation or is there more to the story?See omnystudio.com/listener for privacy information.

Lauren admits she REALLY liked Jason. In fact, she says she would've absolutely gone out with him again if he had handled ONE thing differently after their date. The problem? Jason had absolutely no idea this seemingly innocent moment was secretly determining whether he'd get date number two.See omnystudio.com/listener for privacy information.

Jessica loves her dog. Like... REALLY loves her dog. She thought Matt would find pictures from his birthday celebration adorable, but something about the whole situation apparently gave him a glimpse into his potential future, and he did NOT like what he saw.See omnystudio.com/listener for privacy information.

Natalie has a problem: she got ghosted after an AMAZING first date with Derek. But she also has a confession... she's OBSESSED with Second Date Update and is low-key freaking out that she finally gets to be on the show. When we call Derek and tell him why we're reaching out, his reaction is NOT what any of us expected.See omnystudio.com/listener for privacy information.

This date was technically amazing... and that's exactly why Heather is so annoyed. She and Zach had chemistry, laughed all night, and even kissed. But Heather had seen something before the date started that made the whole night feel VERY different. Zach's explanation only makes things messier.See omnystudio.com/listener for privacy information.