Second Date Update Classic: Cowboy Confu...

<p>We're pitting the generations against each other with the ultimate trivia game, it's Brooke vs. Alexis!</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p> 

<p>Part 1&nbsp;</p> <p>If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say &ldquo;YES!&rdquo;</p> <p>Part 2</p> <p>One of our listeners is a barista and says she did something she would ... Show More

<p>FULL SHOW: Friday, November 21st, 2025</p> <p>Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:</p> <p><a href="https://www.youtube.com/c/BrookeandJeffrey">Youtube</a></p> <p><a href="https://www.instagram.com/brookeandjeffrey/?hl=en">Instagram</a></p> <p><a ... Show More

One of our listeners said she made the first move and left her comfort zone to hit on a handsome guy. That decision lead her here but maybe we can help her finish strong with a Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for pri ... Show More

One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her he had to do THIS first. Find out what it is in your Second Date Update podcast!! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener fo ... Show More

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night! Hear what happened in a new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy in ... Show More

Get your 2nd Date Update Merch For A Cause HERE! The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information. 

There’s one moment in every date where you can end on a high note, or push your luck and risk it all. One of our listeners says he definitely made the wrong choice on his date and now he’s on the line looking for help in an all new Second Date Update! Get your 2nd Date Update Mer ... Show More

When you're out to dinner and you notice something on your date's face, do you tell them or keep it to yourself? One of our listeners is worried the choice he made is why he's not getting a call back. We'll find out in a brand new Second Date Update! Get your 2nd Date Update Merc ... Show More

One of our listeners had not one but TWO opportunities to be a “Knight In Shining Armor” for his date… so why is she ignoring him after his heroism? We’ll try to find out in your Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for p ... Show More

Get your 2nd Date Update Merch For A Cause HERE! One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!See omnystudio.com/listener for privac ... Show More

One of our listener’s first kiss happened but her second date never did! So we’re gonna do everything in our power to get to the bottom of it in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

We were shocked when we heard about our listeners tense situation that went down on a first date with an UNEXPECTED VISITOR… You’ll hear how we help him in a brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for priv ... Show More