Why Modern Marriage Fails and What Couples Can Do About It

Host Tom interviews divorce attorney James Sexton, who brings a uniquely analytical perspective to love and marriage shaped by years of watching relationships fail in courtrooms. Sexton opens by framing relationships as an economy — not in a cynical sense, but as an honorable exchange of value where both parties bring different things to the table. He argues the problem isn't inequality of contribution but rather unspoken tallying of debts and the cultural pressure to make every contribution identical rather than complementary. He uses Steve Jobs and Steve Wozniak as an example of how different but complementary contributions can create something neither could achieve alone.

Sexton challenges the unquestioned assumption that marriage is simply 'what you do,' pointing out that as a technology it fails catastrophically 56% of the time in divorce, and arguably 76% when accounting for miserable-but-intact marriages. He argues this failure rate would prompt serious questioning in any other domain, yet couples rarely ask 'why are we getting married?' before proceeding. He distinguishes between the government-written prenup every married couple has by default and the intentional rule-setting that thoughtful couples should engage in before marrying.

The conversation explores how modern life has deranged the evolutionary incentives for pair bonding. Sexton agrees with Tom's thesis that Western safety and prosperity since WWII has eroded the survival-based reasons for marriage, leaving people confused about what value the institution offers. He also credits the overcorrection away from rigid gender roles — which were genuinely a prison — as having swung so far that any acknowledgment of male-female differences is now treated as heresy, leaving couples confused about expectations.

Sexton argues social media has amplified pre-existing tensions between the sexes through algorithmic enragement, and that advertising — which he calls the opposite of therapy — has bombarded people with the core message 'you are not okay' for decades. He credits his graduate mentor Neil Postman, author of 'Amusing Ourselves to Death,' as prescient about how adding technology to a social ecosystem transforms the entire ecosystem rather than simply adding one new element.

On practical solutions, Sexton advocates for simple weekly check-ins where couples ask each other what made them feel loved and what could have been done better — tools he says cost nothing but are rarely used because we've been told marriage should be effortlessly natural. He uses sex as a case study in how good intentions create problems: couples quickly learn each other's preferences, play the hits, create a routine, and then find themselves bored and dissatisfied — not from malice but from misguided optimization. He argues this pattern of unintentional self-sabotage is endemic to marriage and only preventable through regular communication.

Sexton also validates Tom's point about the power of ritual, agreeing that a wedding ceremony has tremendous symbolic value as a demarcation between one phase of life and another, even if the legal status of marriage itself is less essential. He argues that the wedding — gathering everyone who built you to witness your commitment — is a profound and primal human act, while 'being married' is the harder ongoing work that follows. He closes by arguing that marriage requires bravery, that bravery only exists when you're scared and act anyway, and that the practical tools for maintaining a marriage are simple, cheap, and widely ignored.