Second Date Update: Let's Chalk About It

One of our listeners took his date to a ball game and INSTANTLY she was set off on a bad mood. He doesn’t know what sparked it but we’re on his side and we’re gonna dig in, when we do a Second Date Update!See omnystudio.com/listener for privacy information. 

Every Sunday, we will be hosting 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, June 12th, 2026 Curious if we look as bad as we sound? Follow us @Brooke ... Show More

Part 1 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! Part 2 What do you do when someone suddenly STOPS replying to your texts? One of our listeners did something a little UNUSUAL to ... 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. 

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. 

The guy in today’s Second Date has a strategy for giving a nickname on the FIRST DATE that he swears is undefeated. Hear what it is in the podcast!See omnystudio.com/listener for privacy information. 

<p>Imagine this: You’re casually dating a guy you really like. He makes plans with you on a Monday for the following weekend, and says he’s looking forward to seeing you, and then… SILENCE. Tuesday, Wednesday, Thursday, Friday…no phone calls, no texts, nothing. What does this mea ... Show More

One of our listeners took his date to a quaint, little remote town....and they almost didn’t come back! Find out why in your Second Date podcast!See omnystudio.com/listener for privacy information. 

What do you do when someone suddenly STOPS replying to your texts? One of our listeners did something a little UNUSUAL to get his crush’s attention. Hear what it was in a Second Date Update!See omnystudio.com/listener for privacy information. 

The woman in today’s Second Date has to defend her one weird habit that she swears is NATURAL, but it left all of us shocked.See omnystudio.com/listener for privacy information. 

<p>We go on a date with Alexis Wolfe AKA @nycdatenite to talk all about post-pandemic dating. From getting back out there and going on that first in-person date in over a year, to determining what the best and worst types of places to go on a first date are, we’re covering all of ... Show More

This week we’re taking a look back on “Double Date”. To celebrate Helene’s birthday, Michael treats Jim, Pam and Helene to lunch, and of course, it ends up being a very cringey disaster. Meanwhile Dwight and Andy struggle to outdo each other in nice favors. Angela reads from her ... Show More