Second Date Update Classic: Way Too Natu...

One of our listeners NEVER expected to face the kind of parenting challenge she’s facing, and it all started when ANOTHER mom reached out with a strange proposition. Catch it all in your Awkward Tuesday Phone Call! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.co ... Show More

According to her email, one of our listeners NEVER gets ghosted. She never really goes on dates either, but she did this time and one dude isn’t calling her back so we’re gonna help try and find out why in your Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!S ... Show More

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: Friday, November 6th, 2026 Get your 2nd Date Update Merch For A Cause HERE! Curious if we l ... Show More

How long should a first date last? The couple in today’s Second Date Update had their date last much, much longer than either one of them either expected.See omnystudio.com/listener for privacy information. 

The couple in today’s Second Date went on a date to the fair and they left with a big mystery afoot… We’ll help them sort it out and solve their problem in the podcast!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

 Coming up in today’s Second Date, a woman planned a date that she thought a typical guy might dream about… And somehow, it completely backfired… Find out what went wrong 

The woman in today’s Second Date Update admits she did something a little drastic to make a first impression… and even maybe a little sketchy.See omnystudio.com/listener for privacy information. 

Today's Second Date Update is one of the classic examples… where one person's Grand Romantic Gesture turns out to be another person's Bizarre Circus Nightmare. Hear what Matt did to screw up his date 

 Coming up in today’s Second Date, a woman planned a date that she thought a typical guy might dream about… And somehow, it completely backfired… Find out what went wrong 

Today's Second Date Update is one of the classic examples… where one person's Grand Romantic Gesture turns out to be another person's Bizarre Circus Nightmare. Hear what Matt did to screw up his date 

We had to try our best to get the woman on the phone to tell us the TRUTH about what happened on her date… and it might be the most embarrassing story of the year! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

One of our listeners tried to go the “funny” route for a first date activity and it ended up stinking worse than Brooke’s microwaved lunches. You’ll hear what happened in a Second Date Update!See omnystudio.com/listener for privacy information.