Second Date Update: The Rudy Of Dating

One of our listeners says he got a singular one-word text that let him know he BADLY screwed up his first date. See omnystudio.com/listener for privacy information. 

Every Sunday, we host 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: Tuesday, August 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffr ... Show More

Part 1 Cory took a PLANE FLIGHT to hang out with Alison… but their date left a lot to be desired… We’ll try to fix their future in your Second Date Update podcast! Part 2 One of our listeners took a BOLD step when she made a move on a guy while he was working… and seconds later t ... Show More

One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks its part of why he’s not getting a call back. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

<p>The guy on the phone today told us he&rsquo;s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we&rsquo;ve never tried before! Catch what it is in a new Second Date Update!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a hre ... Show More

Typically on a first date, you’re supposed to do something fun and not invite someone to your work... But the guy in today’s Second Date did the second option and now he’s calling us for help fixing his love life!See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date Update made a BOLD REQUEST before we even called his date. Was it fair? Sure! Was Brooke offended by it? Yep!See omnystudio.com/listener for privacy information. 

Typically on a first date, you’re supposed to do something fun and not invite someone to your work... But the guy in today’s Second Date did the second option and now he’s calling us for help fixing his love life!See omnystudio.com/listener for privacy information. 

Our listener on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material! You’ll hear what it was in your brand new Second Date Update! Get your 2nd Date Update Merch For A ... Show More

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest. Hear the brand new Second Date Update in the podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

The guy on the phone today gets points for a creative first date idea, but his lady disappeared on him and now we’re on the case trying to figure out exactly how he went wrong. See omnystudio.com/listener for privacy information. 

Part 1 The guy in today’s Second Date Update tried a pickup line that was cringey, not just on one level… but on MULTIPLE LEVELS and he quickly realized he needed our help. Part 2 One of our listeners found themselves in the middle of an epic house party and he thinks he found a ... Show More

What’s the opposite of a Wingman? Whatever you call it, that type of guy is what ruined our listeners date.  Now he wants our help to try and save it with a Second Date!See omnystudio.com/listener for privacy information.