Why Dates Go Wrong | Episode 62

In a bit of Podcast Verité the guys break the 4th wall as they launch into a discussion of Why Dates Go Wrong. Meandering, Paul admits to his continued astonishment at being married; he thought of it as something “other people do.” Instead of the marriage stereotypes emblazoned on boardwalk t-shirts - “Game Over” - Paul has found he loves having a playmate to come home to at night. This anticipates a section later in the podcast, in which Paul claims that open communities evaporate by 40; a single, 42-year-old guy has nowhere to go. In their discussion of first date follies, the guys talk about key attributes of a “successful dater”: calm, pragmatic, stoic, not proud, thick-skinned. Paul talks about his days in NYC as a rigid, unyielding dater who reduced “degrees of freedom” to devastating effect. Peter and Paul discuss the perils of the 2nd date and joke that it should be eliminated altogether; more earnestly, they wonder which areas in ourselves we can accept and which we need to improve. Somehow, they get on the topic of frivolous youth and wonder if the iconic billionaires of today have cast a pall over people’s 20’s - a theme we discussed in The Billionaire Bust Up | Episode 14. Later, Pete tells us the #1 Problem in modern dating is too much choice and adds a personal note, joking he’s been the victim of a sympathy date but also that he likes to underperform in the early days to keep expectations in check. Paul is worried about the lack of relationship skills out there among young singletons - one girl Pete knows refuses to date an inexperienced man, saying she doesn’t want him to make his first mistakes on her. Paul understands the Achilles Heel of Mr. Single, dating machine extraordinaire: the inability to properly service a relationship. The transition for Paul was tough, at times, and he finally learned first-hand why IKEA is like kryptonite to single men. Paul pitches his upcoming e-book, On Marriage, and explains his take on the 5 Steps to the Altar: dating, courtship, cohabitation, engagement and marriage. Finally, the guys get nostalgic for youthful spontaneity and Pete worries that logistics will crowd out romance in his future relationships.