Awkward Tuesday: Babysitting Blues
A part-time babysitting job led one of our listeners into our email where she's trying to figure out how to confront her "boss" about how sh...
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Comedy
Brooke and Jeffrey: Second Date Update
Second Date Update - Binge listen to all the Second Date Update's you haven't heard from Brooke & Jeffrey In The Morning. We promise you'll laugh! ‘With’ or ‘At’, we’ll let you be the judge.
Episodes
20 of 2,302 episodesSecond Date Update: The Set Up
Meghan told herself she'd only go out for "one drink" but that night spiraled out of control and now she needs OUR HELP to fix her mistakes...
FULL SHOW: Halloween COSTUME Reveal, Horror Fest Date + Monster (Laser) Stories (10/30/26)
Every Sunday, we host one of our FULL HOUR episodes from our main show feed Brooke & Jeffrey, and incase you missed it, here's our extra spo...
Second Date Update Classics: Real Life Ghosting + Halloween Ghostface Ditcher
Part 1 The couple in today's Second Date Update went to a haunted house for their first date, but only one of them came out, and now HE want...
Second Date Update: Something Sticky Down There
Everyone in the room might have been shrieking at the time but that's the moment Shawn knew he was in love! Can he regather the girl that's...
Reverse Trick or Treating
It has a 0% success rate but that's not gonna stop us! We sent Ashton out for REVERSE TRICK OR TREATING to see if someone will let him into...
Second Date Update: Float & Boat
One of our listeners was SO RELAXED on her night out with Vince, that she did something unintentional and kind of embarrassing. She thinks i...
Awkward Tuesday: Haunting of Boyfriends Past
Today's Halloween Edition of the Awkward Tuesday Phone Call is a mortifying conversation between two people who REALLY don't like each other...
Second Date Update: Haunted House Hero
One of our listeners said he met a woman during the spookiest time of the year but he never expected to be GHOSTED! We're investigating and...
FULL SHOW: Break Room Romeo Date, Jeff’s Busted Birthday + Brooke Goes to the Club (10/21/26)
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...
Second Date Update Classics: Dutch Isn't Just A Language + Dry Lips & Hands On Hips
Part 1 Jake and Kim bonded on their date over their shared HATE for one specific thing… But now she's not calling back? Maybe we can...
Second Date Update: Apple Picking For The 1 Percent
Daniel was DESPERATELY trying to avoid answering one specific question on his date with Lilly. It got asked, it DIDN'T go well, and now he w...
Awkward Thursday: Candy King of the Neighborhood
The guy on the phone for today's Awkward Thursday Phone Call DESPERATELY needs our help because his HOA is threatening to FINE him hundreds...
Second Date Update: Microwaved Salad Guy
One of our listeners has a crush on his co-worker and he came up with a plan to show her! It involves a microwave and a wilted bowl of salad...
Awkward Tuesday Phone Call: No No No Show
Two weeks after tying the knot, Katherine wants an apology from one of her unruly family members for the way he acted at her wedding. Its yo...
Second Date Update: Food Court Cutie
Susan said her date asked her a STRANGE question at the end of the night and was VERY disappointed by her response… You'll hear the q...
FULL SHOW: Jeff’s Ode to Pasta, Overly Romantic Date + Dumbest Healthcare Questions (10/16/26)
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...
Second Date Update Classics: Bathroom 911 + Big Fajita Energy
Part 1 Nick is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman...
Second Date Update: Vacation On Me
Kyle made ONE SLIGHT adjustment to his dating profile and he ended up matching with a woman he calls "The real deal." So why does he need ou...
Second Date Update UPDATE: A Whole New Girlfriend
You may remember Brian and Olivia as a "Disney DO & Disney DON'T" couple where he was super into all things Disney and she was open to learn...