Brooke and Jeffrey

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Latest Episodes:

Awkward Tuesday: A Rabbi Walks Into A Bar Oct 13, 2026

Show notes

Meeting your girlfriend’s parents can be stressful! It happened to Simon over a month ago, so why NOW does he need our help “fixing” what he says went wrong? Find out in a new Awkward Tuesday Phone Call!

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Phone Tap: Fantasy Roommate Oct 13, 2026

Show notes

Have you ever been in a fantasy league where you don’t quite know EVERYBODY in the group? That happened to today’s Phone Tap victim, who is joining a football league with a new group and he’s never met the commissioner until we call him!

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Masked Speaker: Cue Stick Etiquette Oct 13, 2026

Show notes

Today's Masked Speaker says he’ll never forget the night he picked up the sexiest woman he’s ever met... But he's never been able to tell anyone about it, not even his best friend who was at the bar with him.... And there’s a VERY good reason he’s kept this secret all this time...

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Shock Collar Question of the Day (10/13/26) Oct 13, 2026

Show notes

It's a "Jerry-Rigged” edition of Plenty of Twenty!

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FULL SHOW: McLaren Mishap Date, Bookstore Humiliation Loser Line + Missed Connections (10/12/26) Oct 12, 2026

Show notes

FULL SHOW: Monday, October 12th, 2026

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

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Win Brooke's Bucks (10/12/26) Oct 12, 2026

Show notes

Have a knack for trivia? Well, so does Brooke… Try to answer as many questions right as you can in 30 seconds. If you answer more correctly than Brooke, you win 100 bucks! Good luck!

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Missed Connections (10/12/26) Oct 12, 2026

Show notes

We scoured the back pages of Craigslist to find the best (or is it worst?) entries from their Missed Connections section! Whether you're a hopeless romantic or just plain hopeless, this might be the place for you!

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Second Date Update: McLaren Missus Mishap Oct 12, 2026

Show notes

In today’s Second Date Update we found ourselves in the middle of a problem that is WAY out of our price range, even Brooke’s!

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Phone Tap: Clover the Big Brother Oct 12, 2026

Show notes

In your Phone Tap, we call a woman who enrolled her son in the Big Brother program, and we’ve got the perfect big brother for him: ex-special ops soldier, CLOVER!

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Loser Line (10/12/26) Oct 12, 2026

Show notes

Don't give that creep at the bar your number! Slip 'em the Loser Line number instead and we'll play their awful voicemail on the air!

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