Today

Second Date Update: No Snow Show

The woman on the phone today learned the HARD WAY after her date promised to give her a luxurious “experience of a lifetime” that she shouldn’t be so quick to trust. She’s ready to call him out in a Second Date Update! See omnystudio.com/listener for privacy information.

19m 26s

Yesterday

FULL SHOW: Romantic Corndog Date, Brooke’s Theater Debut & José’s Bathroom Encounter (1/28/26)

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, Janu ... Show More

1h 7m

Jan 31

Second Date Update Classics: Sweet Sixteen Dates+ Be Excellent & Be Thirsty

Part 1 There’s a brand new food item that you should definitely AVOID ordering on a first date unless you want to end up like one of our listeners. We’ll hear what it was and try to help him recover in your Second Date Update. Part 2 One of our listeners had not one but TWO oppor ... Show More

38m 18s

Jul 2025

Second Date Update: Randall Is Back For More

After many failed romantic encounters...and a couple of outright scams...one of our most lovable listeners is back! He says this time is different because he finally executed the perfect date night, at least for a few minutes. We'll find out what went wrong this time in your bran ... Show More

16m 54s

Dec 2024

Second Date Update: Happy Shamaversary

One of our listeners tried to go the “funny” route for a first date activity and it ended up stinking worse than Brooke’s microwaved lunches. You’ll hear what happened in a Second Date Update!See omnystudio.com/listener for privacy information.

17m 48s

Jun 2025

Second Date Update: Lonely Cannoli

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

16m 55s

Sep 2024

Second Date Update Classic: Someone's On The Naughty List

After today’s Second Date Update happened we almost DIDN’T AIR IT, but Jeffrey said “the listeners deserve to hear this.” Judge for yourself after hearing the Second Date Podcast!See omnystudio.com/listener for privacy information.

15m 49s

Aug 2025

Second Date Update: Marathon Date

One of our listeners said his date was a 10/10 and going flawlessly, that's why he couldn't believe what happened when he went in for the first kiss...We're gonna hear it in a brand new Second Date Update. See omnystudio.com/listener for privacy information.

17m 7s

Aug 2024

Second Date Update: Dine For One But I'm Not Done

The listener on the phone says her date ended up with some unexpected extra guests… but it’s actually kind of sweet how it all came together. Hear what happened in a Second Date podcast!See omnystudio.com/listener for privacy information.

17m 15s

Oct 2025

Second Date Update Classics: 10 Pin Mixup + Pop Goes the Relationship

Part 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and ... Show More

36m 4s

Oct 2025

Second Date Update Classics: Ex-Aversary + Lady In Red

Part 1 The guy from today’s Second Date Update said he got a text that completely BAFFLED HIM considering how good his first date went...You’ll hear about the weird message he received coming up. Part 2 An interaction on the dance floor led to one of the most embarrassing situati ... Show More

34m 34s

Mar 2025

Second Date Update: Taco Truckstop Mystery

<p>A listener from one of the most popular Second Date Updates of 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!</p><p>See <a href="https://omnystudio.com/listene ... Show More

17m 14s

Sep 2025

Second Date Update UPDATE: Love On The Rocks

Two of our listeners decided to go on a HIKE for their first meetup and it turned into one of the most memorable Second Date Updates of the year! Now they’re BACK with an UPDATE!See omnystudio.com/listener for privacy information.

17m 5s

Second Date Update: Randall Is Back For ...