Second Date Update: Yup Date For Jessica

<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

A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever! Hear what it said coming up in a new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy informa ... Show More

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

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

The couple on the phone today were so sweet and cute the last time they appeared on our show that we’re having them back on for a Second Date Update UPDATE. Stick around through the end to hear what's happened since they last joined us! Get your 2nd Date Update Merch For A Cause  ... 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. 

One of our listeners was DITCHED on a date in a BRAZEN way and so today we’re on the hunt for ANSWERS in your Second Date Update podcast! 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

The woman on the phone today got an INTERESTING surprise when she got into her date's car, and that kind of weirdness is something we can all get behind on this show! New Second Date Update podcast is all yours! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/l ... 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. 

<p>A listener from one of the most popular Second Date Updates of last year is BACK&hellip; the bad news is the guy she went out with is trying to avoid her (he even RAN AWAY). We&rsquo;re gonna try to find out why in the podcast!</p> <p>Get your 2nd Date Update Merch For A Cause ... Show More