Brooke and Jeffrey: Second Date Update

You never know what someone is gonna say when they think no one is listening. One of our listeners overheard their employee say something, and now we have an Awkward Tuesday Phone Call on our hands! See omnystudio.com/listener for privacy information.

This may be the BIGGEST RED FLAG we’ve ever heard on a first date… yet somehow, they still hooked up afterwords??  See omnystudio.com/listener for privacy information.

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, January 23rd, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJe...

Part 1 The guy on the phone today says he managed to pull a woman WAY out of his league, and it's all thanks to ONE move he pulled at the very end of the date!  Part 2 One of our listeners says he doesn’t need help getting a hold of the woman he dated… he needs our help to avoid criminal prosecution instead!  See omnystudio.com/listener for privacy information.

One of our listeners unintentionally did something at the EXACT SAME TIME as his date, and he says it’s a sign of something HUGE! Hear what it is coming up in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

It’s back by popular demand and against Brooke’s better judgment: We’re doing an all new edition of Brooke Breaks You Up! See omnystudio.com/listener for privacy information.

The guy on the phone today is a member of the “first timers club.” What’s the first timers club, exactly? Find out for yourself when we do a Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners says the family she babysits for owes her a lot of money... And because they won't pay up, she's ready to confront them in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners has a unique technique in order to give herself a pick-me-up on a date. And not only did it work for her, it led her to a guy she really likes too! Hear her strategy in your Second Date Update! See omnystudio.com/listener for privacy information.

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: Wednesday, January 14th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok Brookean...

Part 1 A little drawing on a cocktail napkin didn’t go the way our listener planned, and neither did his date night! You’ll understand why in the Second Date Update. Part 2 Just when you thought nothing good happens on airplanes anymore, one of our listeners met a woman on a flight and his story might inspire everyone listening! See omnystudio.com/listener for privacy information.

The guy on the phone today got caught showing up to his date after getting dropped off by ANOTHER WOMAN! We’re readying our battle stations for a contentious Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners asked his date a question that was RUDE, INSENSITIVE, and INAPPROPRIATE… at least we thought at first… Now he’s back for a special Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

Ethan started his night meeting one woman, and ended up with a completely different one at his table by the end of the night! He’s desperate for a Second Date Update and we’re gonna give him one! See omnystudio.com/listener for privacy information.

99.9% of boyfriends would NEVER ask their girlfriends what the guy on the phone today asked his. Now he wants our help with an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

All the guy on the phone today had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself… It backfired and now he wants a Second Date Update!  See omnystudio.com/listener for privacy information.

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, January 9th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJef...

Part 1 One of our listeners didn’t admit her guilty pleasure to her date, she THEMED their entire evening around it. Now she’s not getting a call back?  Part 2 One of the most popular Second Date Updates from last year is BACK… the bad news is the guy she went out with is trying to avoid her (he even RAN AWAY). We’re gonna try to find out why in the podcast! See omnys...

The guy on the phone today 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? Find out in the Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners hopes things aren’t falling apart with his long-distance girlfriend. And with our help he wants to make an Awkward THURSDAY Phone Call! See omnystudio.com/listener for privacy information.

There’s one moment in every date where you can end on a high note, or push your luck and risk it all. One of our listeners says he definitely made the WRONG choice on his date and now he’s on the line looking for help with a Second Date Update. See omnystudio.com/listener for privacy information.

One of our listeners just moved in with her fiancé and what she found buried in his attic was incredible! She needs our advice on how to talk to him about it so we’re doing an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

There’s one thing a guy can put on his dating profile that will instantly up his chances of matching by 90%... The woman on the phone today saw it on her date's profile and now she wants our help locking him down in a Second Date Update! See omnystudio.com/listener for privacy information.

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, January 2nd, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJef...

Part 1 One of our listeners said she added 3 little numbers to her dating profile and it made her matches go through the roof! Find out what it was in the podcast! Part 2 The guy in today’s Second Date Update DID NOT google his date before meeting up with her and sure wishes he did now! Good thing she'll reveal her juicy secret to us.  See omnystudio.com/listener for privacy information...