Awkward Tuesday: Grandpa's Secret Stash
One of our listeners just moved in with her fiancé and what she found buried in his attic was incredible! She needs our advice on how to talk to him about it so we’re doing an Awkward Tuesday Phone Ca...
6 Jan 19min
Second Date Update Classic: High Stakes Higher Stacks
There’s one thing a guy can put on his dating profile that will instantly up his chances of matching by 90%... The woman on the phone today saw it on her date's profile and now she wants our help lock...
5 Jan 17min
FULL SHOW: Anti-Baseball Date, Butter Personality Test + Worst Company Gifts (1/2/26)
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...
4 Jan 58min
Second Date Update Classics: 401 Not Ok + Offline and Oblivious
Part 1 One of our listeners said she added 3 little numbers to her dating profile and it made her matches go through the roof! Find out what it was in the podcast! Part 2 The guy in today’s Second Dat...
3 Jan 36min
#1 Second Date Update of 2025: Don't Take Me Out To The Ballgame
The guy in today’s Second Date Update made a BOLD REQUEST before we even called his date. Was it fair? Sure! Was Brooke offended by it? Yep!See omnystudio.com/listener for privacy information.
2 Jan 18min
Blind Love Is? Tyler and Shauna
Two of our listeners are taking a big risk by being on our show today... in hopes of reaping the BEST REWARD of all... and they're about to meet for the first time over the phone...See omnystudio.com/...
1 Jan 17min
#2 Second Date Update of 2025: Flirt and Observe
One of our listeners says she experienced an intimate moment with a guy she’d never met, when they were in a crowded coffee shop at the same time…and it was definitely more than just flirty eye contac...
31 Dec 202517min
Awkward Tuesday: The Prank That Went Too Far
The woman in today’s Awkward Tuesday Phone Call almost screwed up her whole relationship just for a social media prank video. Things are gonna get messy when we get her on the podcast!See omnystudio.c...
30 Dec 202516min
