In this episode of Modern Wisdom, James Sexton, Rick Glassman, and Matt McCusker discuss relationship dynamics, sexuality, and modern dating trends. Sexton, a divorce attorney, shares insights from his practice about how small gestures maintain connection in relationships and how marriages often end not from dramatic failures but from partners gradually stopping noticing each other. The conversation covers practical topics like addressing physical changes compassionately, the role of prenuptial agreements in modern partnerships, and how biological differences between partners require intentional communication.
The panel also explores shifting attitudes toward sexuality among younger generations, examining statistics on virginity rates, pornography use, and masturbation habits. They discuss the distinction between authentic desire and using pornography as emotional distraction, how erectile function relates to emotional connection, and the lingering effects of religious upbringing on sexual attitudes. Throughout, the conversation highlights gender differences in partner expectations, financial dynamics in relationships, and the importance of direct communication in maintaining healthy partnerships.

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James Sexton shares a story about a client whose marriage ended when her husband stopped buying her favorite granola—a simple, unprompted gesture that had made her feel loved and seen. Sexton emphasizes that spontaneous acts of care carry more value than those done out of obligation, and that marriages often unravel not from dramatic failures but because partners stop noticing small changes. Ben Kissel suggests openly communicating needs rather than waiting in silence, while Sexton stresses that attentiveness is essential to preventing relational decay.
The discussion turns to how partners can address sensitive topics like weight gain compassionately. Sexton advocates for proactively noticing and voicing changes before they become major problems, focusing on health and satisfaction rather than criticism. Both partners should feel empowered to share honest feedback in a supportive way. Sexton also highlights the difference between spontaneous and solicited compliments—unprompted praise feels more genuine and affirming.
Sexton argues that relationship success depends on intentionality and clear communication rather than coasting on default patterns. Early conversations about expectations, including prenups, clarify the framework for partnerships. Addressing issues like declining intimacy or health changes openly helps relationships function better, as dialogue should aim to address problems without signaling overall rejection.
Discussing hormonal cycles and mood fluctuations, Sexton suggests that partners shouldn't point out hormonal changes during the episode itself, as this provokes defensiveness. Matt McCusker adds that in households with children, the male partner maintaining emotional steadiness provides crucial stability when the mother experiences hormonal shifts. Accepting a partner's irrational moments and responding with calm reduces conflict.
Ben Kissel emphasizes that for him, erectile function isn't mechanical—it's about whether he wants to be intimate with someone. He views his erection as an internal signal of genuine emotional connection, saying his body asks, "do you like this person?" Kissel advocates for direct communication before sexual encounters to reduce performance anxiety and pressure. He makes clear that being able to get hard signals trust and comfort, not just physical attraction.
A Playboy survey found that 36% of young adults aged 18 to 29 reported no masturbation in three months, though Kissel views this with skepticism, citing social desirability bias. Chris Williamson notes that 34% of young men say pornography completely satisfies their sexual desire, highlighting how porn substitutes for real intimacy. Sexton points out generational differences in porn access and how saturation via internet and social media impacts young people's expectations and ability to form genuine connections.
Matt McCusker introduces the distinction between "horny"—authentic sexual desire—and "porny"—using pornography to distract from loneliness or negative emotions. Kissel compares "porny" masturbation to eating junk food out of boredom. The conversation explores how masturbation without porn may be healthier, as it avoids reliance on external stimulation that can interfere with emotional wellbeing.
The group discusses the practical aftermath of sex, including the "cum run" to the bathroom. Kissel describes routines for post-coital clean-up as part of a mutual care contract, while Williamson shares his practice of asking about towel preferences. Sexton and Williamson suggest that this unglamorous, practical care distinguishes genuine connection from transactional encounters, building trust and comfort between partners.
Prenups have been enforceable since the 1960s but became popular about twenty years ago as divorce rates rose. Sexton explains that prenup discussions should center on protecting each partner if the relationship ends, recognizing that every marriage ends either by death or divorce. Modern prenups include not only financial protections but also lifestyle and behavioral clauses, such as alimony reductions for weight gain or detailed personal care budgets, particularly demanded by economically independent women.
Wasteful dissipation of marital assets occurs when one spouse irresponsibly spends large sums without the other's consent—examples include $150,000 spent in Las Vegas or excessive luxury purchases. The wronged spouse must prove the spending was wasteful through receipts and bank statements to recover a larger share of remaining assets during divorce.
Sexton observes that women traditionally marry the same or upward economically, while men marry the same or downward, impacting prenup negotiations. Economically independent women now insist on specific personal care budgets in prenups, while female judges are sometimes harsher on women, holding them to stringent standards. The legal system's financial obligations in alimony and child support may trap spouses in unhappy marriages due to economic pressures.
Sexton and Chris Williamson note that cultural messaging tells women they deserve the best partner, while men rarely receive comparable affirmations. Women typically seek financial stability and provider mentality in partners, while men prioritize attractiveness, supportiveness, and kindness—rarely mentioning earning potential. This creates imbalanced expectations where women have longer requirement lists and men are evaluated on narrower traits.
Sexton notes that women have historically been gatekeepers of sex and reproduction, shaping male behavior. He points out that male attraction generally responds to female standards, and much male behavior—including status displays—fundamentally aims at attracting women's attention. The group references how sexual motivation underpins many male pursuits.
Sexton explains that female judges often impose harsher judgments on women than male judges do, criticizing details like courtroom attire. Williamson adds that data shows female judges hand down longer sentences to women on average, indicating internalized bias.
The panel acknowledges that men and women differ emotionally and hormonally, requiring sensitive approaches. Sexton notes that men's anger often masks deeper sadness. McCusker points out that women's hormonal fluctuations strongly affect wellbeing, and couples must accept each other's biological realities without judgment to maintain trust and harmony.
Williamson cites data showing one in five Gen Z adults reports being a virgin, marking a shift from past generations. Among those who've had sex recently, 45% reported just one partner, indicating most activity occurs within committed relationships. The statistic that 36% claim no recent masturbation is questioned by Kissel and Williamson, who suggest social desirability bias leads to underreporting.
Sexton observes a cultural swing toward shaming men for masturbation and pornography consumption, reversing earlier sex-positive messaging. McCusker describes personal disinterest in porn with age, while Sexton warns that renewed sexual shame may harm attitudes toward sexual expression and self-exploration, undermining decades of progress in encouraging healthier conversations about sex.
Sexton details how strict Catholic upbringing suppressed sexual desires and created internal conflicts. Even decades after leaving religion, deeply ingrained shame remains—he still knows the order of Catholic mass by heart. Sexton connects rote religious memorization to how teachings become filters through which intimacy and relationships are processed, often leaving lasting guilt around sexual topics.
1-Page Summary
James Sexton shares the story of a client whose marriage effectively ended when her husband stopped buying her favorite granola, a simple act that had consistently made her feel loved and seen. She used to put the granola on her yogurt every morning, and her husband would always notice when she was running out and buy more without being asked or needing thanks. This spontaneous gesture, done without expectation of reward or acknowledgment, stood as a symbol of genuine care in their relationship. When he stopped, she waited for him to notice, but he didn’t, and she realized the shift marked the decline of their connection—preceding any infidelity.
Sexton emphasizes the importance of these unprompted acts of attention. He draws a symbolic comparison to reciprocated intimacy, stating neither partner "owes" the other such gestures, but a mutual slowing or stopping of affectionate acts signals issues. The group discusses how spontaneous acts of care carry more value than those performed out of obligation or in pursuit of "good boy points." When noticed and reciprocated, meaningful gestures like buying granola or complimenting without being asked foster connection, while noticing their absence early—and communicating concerns before resentment develops—is crucial to preventing relational decay.
Rather than waiting in silence, Ben Kissel suggests openly communicating needs, such as simply asking for more granola and watching how a partner responds. The key, Sexton asserts, is attentiveness: marriages often unravel not due to dramatic failures but because partners stop noticing and responding to small changes. Paying attention and naming these shifts directly is essential.
The discussion turns to physical changes such as weight gain, and how to address these topics compassionately and constructively. Sexton mentions an extreme prenup clause penalizing weight gain, to highlight poor approaches. Instead, he advocates for proactively noticing and voicing changes—like weight, intimacy, or routines—before they become major problems. The aim isn’t to criticize or shame, but to surface what’s happening and explore its impacts together, supporting each other’s wellbeing and attraction.
Both partners, they note, should feel empowered to share honest feedback about changes in themselves and each other, with the understanding that both may undergo shifts over time. Kissel points out there is a value in having a partner hold them accountable in a supportive, non-judgmental way. Physical attraction and health are intertwined; the key is being tactful and focusing discussions on health and satisfaction in the relationship.
Sexton also highlights the dynamic between solicited and spontaneous compliments. There is a qualitative difference between a partner noticing and praising something unprompted versus being asked “Do you think I look pretty in this dress?” Spontaneous compliments feel more genuine and affirming, emphasizing the ongoing importance of attention and care.
Sexton argues that relationship success depends on intentionality and clear communication, rather than coasting on default patterns. Early conversations about the "economics" of a relationship include discussing expectations, obligations, and even prenups—conver ...
Relationship Dynamics and Communication
Sexuality and sexual health encompass emotional intimacy, communication, the ways we seek satisfaction, and the often-unglamorous details of real-life connection.
Ben Kissel emphasizes that for him, erectile function isn't about the mechanical ability to get hard; it's about whether he wants to be hard with someone. He views his erection as an internal signal of genuine emotional connection and comfort, saying, "My penis is basically saying, do you like this person? It's not a moral decision, it's a buddy that's like, Rick, this one's not for you." This view contrasts with James Sexton's experience, who notes that his body often gives mixed or misleading signals about true compatibility.
Kissel explains the importance of direct, unambiguous communication before a sexual encounter. For example, if a potential partner is coming over late at night and the implication is sex, he'll explicitly state that while attraction exists, there's no guarantee of sex, reducing the pressure and the risk of disappointment or performance anxiety. This filtering, according to Kissel, enables both partners to feel safer, fostering trust and comfort.
Kissel makes it clear that being able to get hard isn't about just physical attraction or surface-level appeal, but about feeling emotionally safe and connected. He describes "going hard" as a sign of trust and comfort rather than a simple response to attractiveness, stating, "We don't have to be in love... but I want to feel safe."
A survey by Playboy found that 36% of young people aged 18 to 29 reported no masturbation in the last three months. Kissel and others view this with skepticism, suggesting that social desirability bias is likely at play—he jokes, "There's no way," asserting near universality in masturbation regardless of what surveys report.
Chris Williamson cites that 34% of young men say pornography completely satisfies their sexual desire, highlighting a trend where porn substitutes for real-life intimacy.
James Sexton points out the generational differences in access to pornography, reminiscing about the scarcity and effort it once took compared to today's saturation via the internet and even social media. The proliferation of porn and "porn-adjacent" content on platforms like Instagram increases young people's exposure and potentially conditions sexual expectations, impacting their ability to form genuine connections.
Matt McCusker introduces the distinction: "Are you horny or are you porny?"—"horny" indicating authentic sexual desire, and "porny" pointing to using pornography as a distraction from loneliness or negative emotions.
Kissel agrees, comparing "porny" masturbation to eating junk food out of boredom rather than hunger: "That's chocolate cake when you shouldn't be eating it." He acknowledges its danger and notes the ease of access often leads to using porn for emotional avoidance.
The conversation explores how masturbation without porn is possible and perhaps healthier. McCusker notes that skipping porn can help break reliance, and suggests it's "not queuing the ...
Sex, Sexuality, and Sexual Health
Prenuptial agreements, or prenups, have been enforceable in a real way since the 1960s. However, they only became widely popular about twenty years ago, which James Sexton attributes to the rising divorce rates. As couples became more aware of the likelihood of marital breakdown, they had to choose between having a rule set written by the government or drafting one together through a prenup.
Sexton explains that prenup discussions should be rooted in care—centered on protecting each partner if the relationship ends. The conversation should revolve around what each person needs to feel safe and supported, even in the event of divorce. This reflects a desire to protect each partner’s heart from harm, including from each other, recognizing that every marriage ends either by death or divorce. He emphasizes that financial fairness should consider sacrifices and choices made by each partner, and that neither total forfeiture nor total gain is just. The ultimate goal is for both individuals to leave the relationship feeling safe and without economic disadvantage if things dissolve.
Prenups today have evolved to include not only financial protections but also lifestyle, maintenance, and behavioral clauses. For instance, Sexton shares that some agreements have included provisions such as a reduction in alimony if a spouse gains weight—a clause once enforcing a $50,000 penalty per year for every ten pounds gained. Additionally, more prenups are incorporating detailed lifestyle budgets, particularly at the insistence of economically independent women who may demand specific monthly amounts for personal care and cosmetic expenses during the marriage.
Wasteful dissipation of marital assets is a significant concern in divorce proceedings, referring to one spouse irresponsibly spending large sums from the marital pot without the other's knowledge or consent. Examples include cases where a spouse spends $150,000 to $200,000 in a single night in Las Vegas or purchases excessive luxury items like Birkin bags and shoes.
When such dissipation occurs, the burden falls on the wronged spouse to prove that the spending was wasteful in order to recover part of the marital assets during divorce. Sexton explains that this process is often contentious and involves meticulous presentation of evidence, such as receipts and bank statements, to demonstrate that the money was intended for the partnership but was squandered for personal indulgence. When successful, such arguments can result in granting the injured party a larger share of the remaining marital assets.
Sexton observes pronounced gender dynamics in how prenups are approached and negotiated. Traditionally, women have married the same or upward economically, whereas men often marry the same or downward. This impacts the dynamics of prenup negotiations and the type of demands included.
Economically independent women, in particular, are now more likely to ...
Legal and Financial Aspects of Relationships
The conversation explores how gender shapes expectations and experiences in relationships, attraction, sexuality, and even legal outcomes, highlighting inconsistencies and biases that persist in modern society.
James Sexton and Chris Williamson note that public messaging and internet culture frequently reinforce the idea that women deserve the absolute best in a partner, showering them with messages like "you're a queen," "you're a boss," or "you deserve the best." Sexton points out that men rarely receive comparable affirmations. Instead, men are told to be content if they have any woman, and society rarely tells them "you deserve a queen." This cultural messaging affects relationship dynamics and what each gender expects from a partner.
Sexton discusses how women typically look for financial stability and seek partners who are earners or have a “provider/protector” mentality. As seen in a viral post by Brooke LeBlanc, some women set comprehensive and high standards—such as seeking men who are "post-economic brackets, still hardworking"—that require men to not only be wealthy enough to not need to work but also still motivated. The group points out that the number of men able to meet such stringent criteria is exceedingly small.
Conversely, most men do not prioritize a partner’s earning potential. Sexton observes that if men were asked what they want in a serious relationship, they’d list qualities like attractiveness, thoughtfulness, being supportive, and good with children. Financial success is rarely mentioned. This results in imbalanced partner expectations and often creates a situation where women have longer lists of requirements and men are evaluated on a narrower set of traits.
Sexton notes that historically and culturally, women have always been viewed as the gatekeepers of sex and reproduction. This power shapes male behavior and cultural customs. Taking the example of shaving, Sexton points out that if women collectively decided to stop shaving their legs, men would simply adapt their preferences, underscoring how male attraction generally responds to female standards.
The discussion continues with the idea that much of male behavior—including displaying status symbols like watches and cars—is fundamentally aimed at attracting women’s attention and approval. This is humorously reinforced by references to media, such as a “Futurama” episode where male effort grinds to a halt when sex becomes easily accessible, suggesting that sexual motivation underpins many male pursuits.
The group examines a counterintuitive phenomenon in the legal system: female judges often impose harsher judgments on women than their male counterparts. Sexton explains that, contrary to popular belief among men facing court cases, female judges are frequently "merciless" toward women. He recounts personal experiences where female judges, off the record, criticized women's courtroom attire—such as questioning why a woman seeking alimony would wear expensive Louboutins—something male judges would not typically notice or m ...
Gender Differences in Relationships, Attraction, and Sexual Behavior
Contemporary trends among Gen Z reveal evolving and sometimes surprising attitudes and behaviors surrounding dating, sexuality, and self-exploration. Shaped by shifting social attitudes and lingering cultural influences, this generation’s intimate habits differ notably from past cohorts.
Chris Williamson cites data showing that one in five Gen Z adults reports being a virgin, highlighting a significant shift in behavior compared to previous generations, where rates of virginity among young adults were typically much lower.
Williamson further notes that among those Gen Z individuals who have had sex in the last three months, 45% reported just one partner—indicating most sexual activity is occurring within committed relationships rather than casual encounters.
Another striking statistic from Williamson is that 36% of young adults say they have not masturbated in the past three months. Both Ben Kissel and Williamson question the accuracy of this figure, suggesting that social desirability bias could lead young people to underreport masturbation. Kissel describes the survey sample as flawed, implying that stigma may cause many to conceal their true behaviors.
James Sexton observes a cultural swing back toward shaming men for masturbation and consuming pornography, in contrast to earlier sex-positive messaging that encouraged openness and self-exploration. The current discourse often frames these behaviors negatively, reviving older taboos.
Matt McCusker describes a personal disinterest in watching pornography as he ages, reflecting a potential trend where men either genuinely reduce consumption or feel pressured to claim they are avoiding it. Sexton’s comments, combined with these reports, suggest that men increasingly discuss or even perform giving up pornography, possibly in response to societal pressure.
Sexton warns that a renewed wave of sexual shame—especially around solitary and private sexual expression like masturbation—may harm attitudes toward sexual expression and self-exploration. The hosts suggest this could undermine the gains of past decades in encouraging healthier, shame-free conversations about sex.
Gen Z Dating and Sexuality Trends
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