Second Date Update: Hero to Zero

A part-time babysitting job led one of our listeners into our email where she’s trying to figure out how to confront her “boss” about how she’s been treated! It's your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

Meghan told herself she’d only go out for “one drink” but that night spiraled out of control and now she needs OUR HELP to fix her mistakes in your Second Date Update!See omnystudio.com/listener for privacy information. 

Every Sunday, we host one of our FULL HOUR episodes from our main show feed Brooke & Jeffrey, and incase you missed it, here's our extra spooky Halloween show! FULL SHOW: Friday, October 30th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instag ... 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. 

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. 

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 from today’s Second Date brought his dinner date back to his place, but before the magic could begin.. something tragic happened!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

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

The guy in today’s Second Date tried to come up with a cool date idea, and he did. But once they were there he had to CONSTANTLY say “NO” to his date. Can we help get a “yes” back from her?See omnystudio.com/listener for privacy information. 

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

Part 1 This might be one of the first International Second Dates we’ve ever done! So come take a ride with us in an ultra-classy Second Date podcast. Part 2 A fun activity to go along with dinner is normally a great date... NOT TODAY. The guy on the phone botched his night and no ... Show More

The listener who needed our help with a Second Date shared a juicy detail from their first meetup that had us all floored, but made us promise to not bring it up when we called his date. We’re always up for a challenge though!See omnystudio.com/listener for privacy information.