Second Date Update PODCAST: Craziest First Date Request

Second Date Update PODCAST: Craziest First Date Request

It has taken years and hundreds of second date updates...but we have finally found out the craziest thing that a listener has asked another person to do during a first date...and honestly, we don't think there's ever going to be another request that will top what happened in this second date update. Find out what crazy thing happened by tuning into the PODCAST.

See omnystudio.com/listener for privacy information.

Episoder(1966)

Second Date Update Classics: Driving Miss Laurie + Lick My Neck

Second Date Update Classics: Driving Miss Laurie + Lick My Neck

Part 1 One of our listeners said he changed ONE THING on his dating profile that instantly changed the game for him. He wishes he’d done this years ago and you can hear what it is in the Second Date podcast. Part 2 Out of every Second Date we’ve done this year, today's might be the most MEMORABLE of the bunch.See omnystudio.com/listener for privacy information.

29 Nov 36min

Second Date Update Classic: Cutecumber Couple

Second Date Update Classic: Cutecumber Couple

One of our listeners says he got his inspiration for his dating “MOVE” by watching on video online and gathering the courage to try it himself. Hear what it was in a Second Date podcast!See omnystudio.com/listener for privacy information.

28 Nov 17min

Second Date Update UPDATE Classic: 8 Trees A Trimming

Second Date Update UPDATE Classic: 8 Trees A Trimming

The holidays nearly broke up the couple on the phone today when they first dated a year ago. But now with the yuletide season coming up were going to reconnect with them for a special update!See omnystudio.com/listener for privacy information.

27 Nov 18min

Second Date Update Classic: First Date Redate

Second Date Update Classic: First Date Redate

The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information.

26 Nov 17min

Awkward Tuesday: Stop That Ugly Duckling

Awkward Tuesday: Stop That Ugly Duckling

Is it ever okay for a person to meddle in their friends love life? It doesn’t matter because we’re doing it anyway before one listener's friend can go on a blind date!See omnystudio.com/listener for privacy information.

25 Nov 19min

Second Date Update Classic: Red Flaggy Much?

Second Date Update Classic: Red Flaggy Much?

One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!See omnystudio.com/listener for privacy information.

24 Nov 18min

FULL SHOW: Jeff’s Iconic Thanksgiving Song, Turkey Day Mishaps + Late & Petty Date (11/21/25)

FULL SHOW: Jeff’s Iconic Thanksgiving Song, Turkey Day Mishaps + Late & Petty Date (11/21/25)

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 feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, November 21st, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

23 Nov 1h 5min

Second Date Update Classics: Date Night Detour + Barista Foam Job

Second Date Update Classics: Date Night Detour + Barista Foam Job

Part 1 If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say “YES!” Part 2 One of our listeners is a barista and says she did something she would NEVER normally do… but taking that risk got her a date with a hot customer and now she wants our assistance bringing him back one more time!See omnystudio.com/listener for privacy information.

22 Nov 37min

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