Second Date Update – “Obsessed with the Ex?”

10/10/2025 47 min
Second Date Update – “Obsessed with the Ex?”

Listen "Second Date Update – “Obsessed with the Ex?”"

Episode Synopsis


CALLER BACKGROUND: SHANNON’S SIDE Shannon confident the date went well.No kissing or overt romantic moments, but the vibe felt good.Craig said, “Hit me up” at the end — Shannon took that as an invitation.She didn’t want to seem desperate, so she turned to the show for help. REACHING OUT TO CRAIG Kevin calls Craig, who agrees to talk (a little reluctantly).Hosts explain the segment and Shannon’s perspective.Craig shares he’s not interested in a second date — “not a fit.”Hosts probe: “What happened?” CRAIG’S REASON: RED FLAGS Craig says Shannon was fixated on his ex.Asked many questions: Who she was, what she looked like, why they broke up, did he cheat, etc.Felt like it lasted 15+ minutes.He wants to focus on the present, not dwell in the past.Said it gave him “a weird vibe.”THE CONFRONTATION: SHANNON JOINS THE CALL Shannon joins the line — surprised and confused.She argues that asking about an ex is normal for getting to know someone.Defends her questions as trying to understand Craig’s background.Craig stands firm — felt like interrogation, not conversation.Shannon insists it wasn’t “trauma dumping,” just curiosity.DEBATE: WHO’S IN THE RIGHT? Craig thinks it was obsessive; Shannon thinks it was reasonable.Shannon accuses Craig of avoiding the topic because he might still have feelings for his ex.Craig disagrees — he just wanted to move forward, not backward.Hosts question both sides: Is it okay to ask about exes on a first date?CLOSURE Hosts ask Craig if he’d consider another date if the ex talk was off the table.Craig declines: “Cat’s out of the bag. It already happened.”Shannon disappointed but thanks the hosts.Both wish each other well.HOSTS RECAP + COMMENTARY Hosts reflect on:The fine line between curiosity and interrogation.Whether it’s appropriate to dig into someone’s past on a first date.Importance of reading social cues and knowing when to move on.Some empathy for both sides: curiosity is human, but timing matters.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.