logo
episode-header-image
Apr 2025
16m 20s

Awkward Tuesday: In Greg We Trust

iHeartPodcasts
About this episode

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey',  that may have even more drama than a Second Date Update. Let us know what you think! 

What happens when you go on 3 dates and one person is CLEARLY wayyy more into it than the other? One of our listeners is in that exact situation and they emailed us for an Awkward Tuesday Phone Call!

See omnystudio.com/listener for privacy information.

Up next
Jul 18
Second Date Update Classics: Offer He Can't Refuse + Sea Meat Surprise
Part 1 One of our listeners says a DEAFENING silence happened after an awkward question from their waiter on their date, and now she’s not getting a call back. Part 2 The woman on the phone today claims that she discovered a place that is swarming with career driven, high-value m ... Show More
35m 57s
Jul 17
Second Date Update: Bidding On Brandy
See omnystudio.com/listener for privacy information. 
18m 31s
Jul 16
Awkward Thursday: Convince The Sis
One of our listeners BROKE UP with a guy and now she’s thinking she made a mistake. She wants him back but before she can get to him she’ll have to go through his SISTER in your Awkward Thursday Phone Call!See omnystudio.com/listener for privacy information. 
18m 52s
Recommended Episodes
Apr 2025
Awkward Tuesday: 15 Minutes of Gurt
How do you tell someone you love that their wildest dream might not be achievable? One of our listeners has that very problem with her boyfriend and she chose to email us for an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 
16m 17s
Jun 2025
Second Date Update Classics: Vacation Date Gone Wrong + Old Flame New Burn
Part 1 Brooke has seen a lot in her 400 years in radio, but today one of our listeners put her in the most DRAMATIC and UNCOMFORTABLE situation of her entire career. Part 2 There’s some topics you just don’t bring up on a first date. One of our listeners didn’t follow that rule a ... Show More
36m 7s
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
Aug 2024
Awkward Tuesday: Ex So Nice Dumped Her Twice
Can you breakup with someone and NOT leave them hating you? We're going to help a listener try to pull it off in today's Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 
14m 48s
Jun 2025
Awkward Tuesday: Prenup or Pre-NOPE
One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 
17m 30s
Sep 2022
Ep 75: Does sexting give you the ick?
tail spinning
30m 8s
Mar 2025
Blind Love Is? Fan Favorite: Doll Beds
We're adding a little extra content to help you get over the Sunday Scaries! Two of our listeners will test the waters and see if they connect romantically when they speak to each other for the first time on our show!See omnystudio.com/listener for privacy information. 
14m 48s
Oct 2025
Awkward Tuesday: Tinder Surprise
One of our listeners asked us for help with an Awkward Tuesday Phone Call but ended up BLINDSIDING us and his girlfriend at the same time. You gotta hear it in the podcast!See omnystudio.com/listener for privacy information. 
17m 24s
Jun 2025
Second Date Update Classics: Hoping For A Bad Date + Nathan Of The Night
Part 1 A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your Second Date Update. Part 2 The entire show was very surprised by how today’s Second Date finished. And we think all ou ... Show More
36m 27s
Sep 2025
Second Date Update Classics: Italian Surprise + Mid Hookup
Part 1 One of our listeners said she met a guy the other night who almost got her ARRESTED. So why does she want another date with him?? Time to find out! Part 2 The woman on the phone says both she AND her date were asked to leave bar trivia over the most ridiculous reason, but ... Show More
36m 38s