Second Date Update Classics: Yup Date For Jessica + 1 Year Later To Rejection King
Part 1 A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever! Part 2 One of our listeners wishes she could take back what she s...
18 Apr 37min
Second Date Update Classic: My Wing Mom
The guy on the phone today got an EMERGENCY call on the way to his date, and it put him in a definite lose-lose situation. Tell us what you would have done, once you hear the Second Date Update!See om...
17 Apr 18min
Textual Healing: A Different Type of Ghosting
In a new relationship there’s tons of little things that could give you the “ick.” We’re gonna help one of our listeners navigate AWAY from those icebergs with some Textual Healing!See omnystudio.com/...
16 Apr 19min
Second Date Update Classic: Hot Date Hijack
What started as a romantic one on one date ended with one of our listeners sandwiched between three gorgeous women all night. He’ll explain how he did it coming up in your Second Date Update!See omnys...
15 Apr 17min
Awkward Tuesday: My Brothers Wife Is A Bad Boss
One of our listeners needs our advice on how to turn someone down. But it’s not just anyone… it’s someone in their own family! We’ll explain more in an Awkward Tuesday Phone Call!See omnystudio.com/li...
14 Apr 17min
Second Date Update: Rez Is Back
What do you do if you’re the ONE PERSON who didn’t get the memo that you’re supposed to bring a gift to the party? One of our listeners had a GENIUS save when that happened to him and it even got him ...
13 Apr 18min
FULL SHOW: Mom’s Night Out Date, Brooke’s Family Secret + Alexis’ Boozy Mexico Lesson (4/8/26)
We're trying out a new idea for our fans of the 2nd Date Update! 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 feedba...
12 Apr 1h 5min
Second Date Update Classics: The First Five Seconds + Hang Up On Him
Part 1 When you're out to dinner and you notice something on your date's face, do you tell them or keep it to yourself? One of our listeners is worried the choice he made is why he's not getting a cal...
11 Apr 37min
