Second Date Update: Let's Chalk About It

One of our listeners is CERTAIN that the universe was talking to her when she met her DREAM MAN. The only problem? They kind met during a disaster and now she wants our help cleaning up after it! It's your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy informa ... Show More

The woman in today’s Second Date Update knows she didn’t give strong signals to the guy she’s interested. In fact, she stayed FAR AWAY from him the whole night! We’ll dig into why in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

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: Thursday, September 10th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJ ... 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. 

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. 

One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks its part of why he’s not getting a call back. Get your 2nd Date Update Merch For A Cause HERE!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. 

<p>The guy on the phone today told us he&rsquo;s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we&rsquo;ve never tried before! Catch what it is in a new Second Date Update!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a hre ... 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. 

The guy in today’s Second Date was so smooth with his pickup line that it impressed all of us in studio. He made the first move but can we help him finish the job?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

In today’s Second Date Update, we spoke to a guy who’s being blown off… And none of the hosts understand why he’s getting stood up… Is there something he’s not telling us? 

In today’s Second Date Update, we spoke to a guy who’s being blown off… And none of the hosts understand why he’s getting stood up… Is there something he’s not telling us?