Second Date Update: Age Is Just A Bummer

<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

<p>Imagine being on a date and the server points out your BIGGEST insecurity&hellip; It happened to one of our listeners and you can hear what it was coming up in your Second Date Update podcast!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a href="https://www.theshopf ... Show More

Running into the last person you would ever want to see while out on a date is a nightmare. It happened to one of our listeners and it might be one of the cringiest Second Dates we’ve ever done!See omnystudio.com/listener for privacy information. 

One of our listeners isn’t sure if his date MEANT to VANISH or if there was just miscommunication but you can tell us what you think after a new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners planned a first date to last 5 full days with a woman he had never even met before! We’ll hear what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

In today’s Second Date Update we had a listener caught in the most awkward position you could hope to be in on a first date. Find out what it was in the podcast!See omnystudio.com/listener for privacy information. 

We had a problem with today’s Second Date Update that we’ve NEVER experienced before and it probably says a lot about why one of our listeners is asking us for dating help.See omnystudio.com/listener for privacy information. 

You won’t believe what one listener pulled off while on her date. Jose was FREAKING OUT that it was even possible! Hear for yourself in the Second Date Podcast!See omnystudio.com/listener for privacy information. 

One of our listeners left his date with a GIFT that was ONLY supposed to be opened the next day… you’ll hear what it was, and how it backfired coming up in the Second Date Update podcast!See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date Update flew across the ocean just to meet someone he think MIGHT be the ONE. Find out what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners said probably the #1 thing you should NEVER EVER say on a first date… No wonder he needs our help, but we’re ready in your Second Date Update podcast!See omnystudio.com/listener for privacy information.