Awkward Tuesday: Ship My Situationship

Blake didn’t spend ANY money on his date with Ashley, in fact, he actually MADE money in a way that’s 100% legal. You’ll hear how in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

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, May 29th, 2026 Curious if we look as bad as we sound? Follow us @Brookea ... Show More

Part 1 One of our listeners realized she’s been approaching dating apps the wrong way… and one piece of advice completed shifted her romantic life. Part 2 The kiss that happened at the end of our listener's date was either the cutest, most spontaneous thing ever, or the cringiest ... Show More

One of our listeners had her daughter come home in tears and she says the only way to fix it is if we helped her a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information. 

<p>One of our listeners secretly contacted her date’s MOM before even meeting up with a guy. You’ll hear her devious plan in a Second Date Update podcast!</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p> 

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not calling back!See omnystudio.com/listener for privacy information. 

One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too! Hear what happened in a Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners admits SHE did something stupid, just to MEET a guy. Was it her idea? No. Was it effective? Find out in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners says it took her less than 12 hours from meeting a guy to completely ruining her chances. Find out how she did it coming up in your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information. 

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. 

After turning down her boyfriend's first proposal....One of our listeners wants our help getting him back on the phone... And re-doing one of her biggest life moments.See omnystudio.com/listener for privacy information. 

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. 

One of our listeners is on the line to tell us about the SURPRISE LOCATION he brought a woman to to try and win her over. Hear where it was in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information.