Second Date Update: Red Envelope Regret

Second Date Update: Red Envelope Regret

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FULL SHOW: Chicken Tender Lovin Date, José's a Dad? + Alexis’ Gross Plane Emergency (2/25/26)

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Wednesday, Febr ...  Show more

Second Date Update Classics: Right To Remain Sexy + Scooter Safety Patrol

Part 1 One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks it's part of why he’s not getting a call back. Part 2 The guy on the phone today had a run-in with a woman who wouldn’t stop SCREAMING at him during his first da ...  Show more

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Second Date Update Classic: Red Envelope Regret
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If only finding a date was as easy as ordering your favorite drink. One of our listeners had the perfect girl right in front of him all thanks to a new dating event that even YOU might want to try! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for pr ...  Show more

Second Date Update: I Hope It's You
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One of our listeners tells us she had an “intense moment” on her date, but it was a GOOD intense. So good, she’s desperate to get a Second Date Update with us!See omnystudio.com/listener for privacy information. 

Second Date Update Classics: Hoping For A Bad Date + Nathan Of The Night
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Part 1 A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your Second Date Update. Part 2 The entire show was very surprised by how today’s Second Date finished. And we think all ou ...  Show more

Second Date Update Classics: 2nd Chance Scott + Mysterious Wallet Situation
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Part 1 One of our listeners took a woman on a BEACH DATE and he gets huge props for one thing he DIDN’T DO… what was it? We're going to find out! Part 2 Today’s Second Date Update might involve one of the GREATEST SCAMS we’ve ever heard on a first date… Hear for yourself in the p ...  Show more