Second Date Update: Halloween Boos and B...

The woman we call in today’s Awkward Tuesday Phone Call might be the most brutal, ruthless, and vile person we’ve ever had on the show. She’s the sister of one of our listeners and we can’t believe what happened when he called to apologize to her!See omnystudio.com/listener for p ... Show More

Andre managed to cancel plans on Kim NOT ONCE, but TWICE in the same night. Is that too much to come back from? Find out in your Second Date Update podcast!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, July 3rd, 2026 Curious if we look as bad as we sound? Follow us @Brookea ... Show More

<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

No party is better for random makeouts than a Halloween Party! One of our listeners was close to getting lucky but fate (or something else) intervened and now she needs a Second Date Update!See omnystudio.com/listener for privacy information. 

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night! Hear what happened in a new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy in ... Show More

What are the odds that the person you meet at a Halloween party would be your PERFECT costume match?? It happened to one of our listeners and you can hear about their outfits in a brand new Second Date podcast!See omnystudio.com/listener for privacy information. 

<p>One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You&rsquo;ll hear it in a brand new Second Date Update podcast!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a href="https://www.theshopforward.com/collection ... Show More

When the listener on the phone described his date we got some creepy vibes. Are we reading the situation wrong or is he just misunderstood? Find out in a new Second Date podcast!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. 

One of our listeners is on the line to tell us about the SURPRISE LOCATION he brought a woman to to try and win her over. Hear where it was in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners was DITCHED on a date in a BRAZEN way and so today we’re on the hunt for ANSWERS in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners was brave enough to introduce his date to his FAMILY on night one! Hear all about this bold new strategy in the Second Date Update podcast!See omnystudio.com/listener for privacy information.