Second Date Update Classic: Halloween Role Reversal

Second Date Update Classic: Halloween Role Reversal

The guy on the phone today wants to try and recreate his perfect first date all over again… exactly one year to the day. It involves wearing children’s costumes and it’s happening in a Second Date Update!

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Episoder(2302)

Awkward Tuesday: Babysitting Blues

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 she’s been treated! It's your Awkward Tuesday Phone Call!See o...

3 Nov 18min

Second Date Update: The Set Up

Second 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 in your Second Date Update!See omnystudio.com/listener for p...

2 Nov 18min

FULL SHOW: Halloween COSTUME Reveal, Horror Fest Date + Monster (Laser) Stories (10/30/26)

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 spooky Halloween show! FULL SHOW: Friday, October 30th, 2026 Cu...

1 Nov 1h 3min

Second Date Update Classics: Real Life Ghosting + Halloween Ghostface Ditcher

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 wants our help getting ahold of the woman! Part 2 No party is be...

31 Okt 36min

Second Date Update: Something Sticky Down There

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 been ghosting him? Find out in your Second Date Update!See o...

30 Okt 18min

Reverse Trick or Treating

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 their home!See omnystudio.com/listener for privacy informati...

29 Okt 17min

Second Date Update: Float & Boat

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 it’s probably why she needs our help with a Second Date Updat...

28 Okt 19min

Awkward Tuesday: Haunting of Boyfriends Past

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 anymore!See omnystudio.com/listener for privacy information...

27 Okt 19min

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