James, a high-profile divorce lawyer, sits down with the host (Stephen) shortly after Stephen’s engagement to discuss how to avoid the most common pitfalls that destroy marriages. James has spent 25 years facilitating the demise of marriages and draws on that experience to offer blunt, practical advice about what actually keeps couples together and what quietly tears them apart.
The State of Love and Connection Today
Society is hungry for real connection more than ever, especially after the pandemic, but has fewer useful tools for finding it and sustaining it.
There is a widespread cultural assumption that love should be effortless, fueled by romanticized portrayals in film, television, and social media. This sets couples up to interpret any discomfort or effort as a sign they are with the wrong person.
James argues this is a false binary: relationships are not supposed to be effortless, nor are they supposed to be drudgery. They require attention, and attention is not the same as hard work.
The Number One Reason Marriages Fail
The most common reason James sees women leave men who are otherwise great providers and protectors is that the woman stops feeling seen and prioritized. She slips in the ranking of what is important to her partner.
This is not usually about grand betrayals. It is about small, gradual disconnections, what James calls “slippage,” tiny moments of neglect that accumulate over time.
The antidote is simple but requires consistency: regular check-ins, even brief ones. A one-minute FaceTime, a text saying “I was thinking of you,” or a quick call between meetings. The content matters less than the signal that the partner is still front of mind.
Why People Avoid the Conversations That Matter
Most people recognize slippage when it is happening but avoid addressing it because they fear temporary discomfort more than they value long-term connection. Our aversion to pain consistently outweighs our desire for joy.
There is also a deep, often unspoken terror that we are not worthy of love, that if our partner truly saw all our flaws and weaknesses, they could not love us. This fear makes exercises like “tell me three things you love about me” feel threatening rather than bonding.
James notes that even high-achieving, successful people are just as bad at this as anyone, because professional competence does not translate into relational skill.
How to Talk About Problems Without Starting a Fight
The way a concern is raised determines whether it leads to connection or conflict. An accusatory framing (“you never listen to me”) triggers defensiveness. A curious, non-blaming framing (“I’ve noticed the tone of our fights has changed, have you noticed that?”) invites dialogue.
James uses a technique in his legal practice that translates directly to relationships: when an opposing lawyer comes at him aggressively, he apologizes first. This disarms the other person and opens space for a calmer exchange.
He suggests couples adopt a “menu” approach: when a partner is upset, explicitly ask what they need in that moment, whether it is listening, solutions, distraction, physical affection, or a walk together.
The Weekly Ritual That Can Save a Marriage
James recommends that every couple, once a week, tell each other three things they love about their partner (different each week), three things the partner did that week that made them feel loved, and three things the partner could have done better.
An optional addition: three things the partner did that week that made them feel desire.
This can be done in writing (text or email) to reduce pressure. James argues that if someone cannot name three things they love about their partner, the problem is not articulateness; it is avoidance rooted in fear of intimacy.
He compares this to exercise: it may feel awkward or uncomfortable at first, but pushing through the discomfort is what builds strength. Avoiding it guarantees decline.
How Childhood Shapes Our Ability to Love
James shares openly about his own childhood: his father was a serious alcoholic, and his mother was consumed by managing that. When young James expressed needs, he was often shamed for them.
This produced a deep need for independence and control, and a terror of asking for help. He became highly competent at almost everything as a survival mechanism, but that same competence became the greatest obstacle in his intimate relationships.
He spent his 30s and 40s trying to eliminate the soft, emotional, empathetic part of himself, believing that the “machine” version of him was the one that would succeed. He eventually realized that both aspects are authentic and necessary, and that the empathetic side actually makes him a better lawyer and advocate.
He encourages people to make peace with the younger version of themselves that still carries fear and loneliness, acknowledging that voice without letting it drive.
The Danger of Glorifying Independence
Many people, especially those who had to be self-reliant early in life, build what James calls “a castle with a moat.” They become so independent that they struggle to let anyone in.
Society reinforces this by glorifying independence and treating dependency as weakness. But lasting connection requires a willingness to need someone and to let them need you.
James’s own journey involved learning that his softness and his drive are not warring forces but complementary aspects of a whole self.
Why Prenups Strengthen Rather Than Weaken Marriages
James is a strong advocate for prenuptial agreements, not because he expects marriages to fail, but because a prenup forces couples to have honest conversations about money, safety, and expectations while they are still in a state of love and optimism.
Without a prenup, the state decides the rules of asset division in a divorce, often using arbitrary thresholds (such as seven years of co-mingling in some jurisdictions) that can create perverse incentives.
A prenup creates three clear buckets: yours, mine, and ours. It defines in advance what belongs to whom, which actually gives couples more control and clarity.
James uses a bag of M&Ms as a visual demonstration: separate property stays separate, joint property is clearly defined, and the rules are agreed upon intentionally rather than imposed by the state.
If the idea of discussing a prenup feels terrifying, that itself is useful information: it means the couple needs to practice having hard conversations before marriage, because life will require many more of them.
Prenups can also be tailored to different life scenarios, such as whether or not the couple has children, and can be updated over time.
Petnups: Planning for the Animals You Love
James created trustedpetnup.com, a free resource for couples (married or not) to establish rules for who gets the pet in the event of a breakup.
Pets are increasingly treated like family members, and disputes over them can become as contentious as child custody cases. A petnup establishes in advance how medical decisions will be made, who gets the animal if the couple separates, and how end-of-life decisions will be handled.
The Divorce Rate, Gray Divorce, and Generational Shifts
The overall divorce rate is slowly rising again after a pandemic-era dip. However, the marriage rate is also declining, and people are marrying later.
Millennials and Gen Z are divorcing less, possibly because they cohabit first, marry later, and enter marriage with more realistic expectations.
“gray divorce” (divorce over age 50) has doubled since 1990 and tripled for those over 65. Contributing factors include longer lifespans, better health and sexual function in later years, women’s greater financial independence, and reduced social stigma around divorce.
James does not view the destigmatization of divorce as negative. Sometimes the healthiest choice is to acknowledge that a relationship is no longer working and to part ways.
The Two Dangerous Assumptions Newlyweds Make
James warns against two seemingly contradictory but equally dangerous beliefs: first, that marriage will change the other person (he will calm down, she will stop worrying); second, that nothing will change and the relationship will stay exactly as wonderful as it is now.
The healthiest stance is to expect that some things will change and some will not, and to keep talking about those changes openly, without judgment, as they happen.
The Promise That Matters Most
James’s deepest wish for any couple is that when the marriage ends, whether in death or divorce, each person can say: “This person helped me become the most authentic version of myself, and they are still my favorite person.”
He defines the purpose of a partnership not as one person becoming what the other wants, but as each person helping the other become their most authentic self, seeing blind spots the other cannot see, and loving the core of who that person is.
He closes by reflecting on a dream he had about his mother, who died ten years ago. In the dream, she sat silently beside him, patting his leg, while he talked. He woke with a powerful sense that sometimes presence matters more than words, and he has since tried to simply be with the people he loves without needing to fill the silence.
