Brooke and Jeffrey: Second Date Update

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!

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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!

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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

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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 better for random makeouts than a Halloween Party! One of our listeners was close to getting lucky but fate (or something else) intervened and now she needs a Second Date Update!

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The guy on the phone today says he found love while in a room full of people shrieking in terror! Now he's called us to help Frankenstein them back together during a special HALLOWEEN THEMED Second Date Update!

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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!

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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 Update!

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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!

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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 digging in for him in your Halloween Second Date Update!

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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 send all negative reviews to Jeffrey.

FULL SHOW: Wednesday, October 21st, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

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https://www.brookeandjeffrey.com/

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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 get her to explain coming up in your Second Date Update!

Part 2

All Anthony had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself…and of course it completely backfired.

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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 wants our help figuring out how to put the pieces back together in your Second Date Update!

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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 of dollars if he goes through with his favorite Halloween tradition!

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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…

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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 your Awkward Tuesday Phone Call!

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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 question and her answer in your Second Date Update!

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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 send all negative reviews to Jeffrey.

FULL SHOW: Friday, October 16th, 2026

Curious if we look as bad as we sound? Follow us @BrookeandJeffrey:

YouTube

Instagram

TikTok

https://www.brookeandjeffrey.com/

See https://omnystudio.com/listener for privacy information.

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 he loves. Will it be worth the humiliation?

Part 2

We have NO IDEA who we’re dialing in today’s Second Date Update, we have a number, and a sneaking suspicion it might be a trap but only one way to find out!

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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 our help? We’ll figure it out in your Second Date Update!

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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 learning more…. But where are they now MONTHS after they first appeared on the show? Find out in your Second Date Update UPDATE!

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