Second Date Update: Just A Little Short

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

There’s a thin line between sharing and OVER-sharing. One of our listeners wished she had learned that lesson BEFORE texting her guy after their date then we wouldn’t be in the position to help her with a Second Date Update!See omnystudio.com/listener for privacy information. 

Part 1 The woman on the phone today saw a cute guy and although her first move was UNORTHODOX… apparently it worked! Part 2 There’s a thin line between sharing and OVER-sharing. One of our listeners wishes she had learned that lesson BEFORE texting her guy after their date... the ... Show More

After today’s Second Date Update happened we almost DIDN’T AIR IT, but Jeffrey said “the listeners deserve to hear this.” Judge for yourself after hearing the Second Date Podcast!See omnystudio.com/listener for privacy information. 

One of our listeners is worried her gratitude for a gift was BADLY misinterpreted as rude and now she wants our help with a Second Date Update!See omnystudio.com/listener for privacy information. 

Our listener on the phone today says his date set a boundary before they even met in person. He had to say “yes,” to get a shot at her, and now we’re trying to get her to say “Yes” to a Second Date!See omnystudio.com/listener for privacy information. 

<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

Part 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and ... Show More

Part 1 One of our listeners tells us she had an “intense moment” on her date, but it was a GOOD intense. So good, she’s desperate to get a Second Date Update with us! Part 2 The woman in today’s Second Date Update might have divulged a little TOO MUCH when she was asked about her ... Show More

One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too! Hear what happened in a Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners invited her date back to her place and spent HOURS together… but what she saw him do… she’s STILL trying to process. Hear what she went through in a new Second Date Update!See omnystudio.com/listener for privacy information.