Second Date Update: Lonely Cannoli

FULL SHOW: Wednesday, July 9th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

Have a knack for trivia? Well, so does Brooke… Try to answer as many questions right as you can in 30 seconds. If you answer more correctly than Brooke, you win 100 bucks! Good luck!See omnystudio.com/listener for privacy information. 

One of our listeners claims they’ve discovered the GOLDEN pick-up line, hear what it is in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a brand new Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners THOUGHT he had a second chance all lined up with his date, but a single one-word text message brought that reality crashing down. Hear what it was coming up 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 tried to go the “funny” route for a first date activity and it ended up stinking worse than Brooke’s microwaved lunches. You’ll hear what happened in a Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners decided his goal was to bring the magic of RomComs to his dating life. You’ll find out how during an all new Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners had a GREAT first encounter with his date, but it was his FIRST TEXT after it ended that wrecked things… Hear what he sent coming up in your Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners met a guy on a trip to the Carribbean, and now she needs our help tracking him down for an INTERNATIONAL SECOND DATE UPDATE!See omnystudio.com/listener for privacy information. 

After one of our listeners met a man on a unique dating website she swears she CAN’T let him slip away! We’ll help her with a Second Date podcast!See omnystudio.com/listener for privacy information. 

Our listener on the phone today says he has a method to getting off the dating apps fast and making an in person date ACTUALLY happen...We're going to hear his strategy and how it played out for him in a brand new Second Date Update!See omnystudio.com/listener for privacy informa ... Show More

One of our listeners said he opened the trunk of his car and his date wouldn’t stop SCREAMING… was it good screaming? Bad screaming? Find out in a brand new Second Date UpdateSee omnystudio.com/listener for privacy information.