Benjamin Franklin wasn’t just a founding father and inventor – he was also America’s original relationship advisor. In 1745, he penned what might be history’s most controversial dating advice in a letter titled “Advice to a Young Man on the Choice of a Mistress.” While encouraging marriage as the ideal path, Franklin offered eight surprisingly practical reasons why older women made better companions than younger ones. His candid observations reveal timeless truths about relationships that still ring true today.
Experience brings better conversation skills
Franklin’s first point focused on intellectual compatibility. He argued that older women possess “more Knowledge of the World” and their minds are “better stor’d with Observations,” making their conversation “more improving and more lastingly agreable.” This wasn’t just about small talk – Franklin valued deep, meaningful exchanges that could stimulate the mind. When someone has lived through more experiences, traveled different paths, and encountered various challenges, they naturally develop a richer perspective on life.
Modern dating often proves Franklin’s point. Someone in their thirties or forties has likely navigated career changes, family dynamics, financial ups and downs, and personal growth that younger people haven’t experienced yet. They can discuss everything from classic literature to current events with depth and nuance. This creates relationships built on genuine connection rather than surface-level attraction. The ability to engage in stimulating conversation becomes increasingly valuable as initial physical attraction naturally evolves over time.
Character development comes with age
Franklin’s second observation was remarkably insightful: “when Women cease to be handsome, they study to be good.” He noticed that older women compensate for diminishing physical beauty by developing their character and usefulness. They learn to “do a 1000 Services small and great” and become “the most tender and useful of all Friends when you are sick.” This transformation from relying on looks to developing genuine value created what Franklin called lasting “amiableness.”
This principle extends beyond romantic relationships into all aspects of life. People who can’t coast on youthful appearance often develop stronger emotional intelligence, better communication skills, and more reliable character traits. They learn to be genuinely helpful, whether that means knowing how to prepare comfort food when someone’s ill or offering practical advice during tough times. Franklin concluded that “there is hardly such a thing to be found as an old Woman who is not a good Woman,” suggesting that life naturally refines character in positive ways.
No unexpected pregnancy complications
Franklin’s third point was refreshingly practical: “there is no hazard of Children, which irregularly produc’d may be attended with much Inconvenience.” In his era, unmarried pregnancy carried severe social and economic consequences. Women faced social ostracism, financial hardship, and limited options for support. Men could also face significant responsibilities and social censure. Older women, particularly those past childbearing years, eliminated these concerns entirely.
While modern contraception has changed this dynamic considerably, the underlying principle remains relevant. Relationships with older women often involve less pressure around family planning decisions. Many older women have already raised children or made peace with their reproductive choices. This can create more relaxed relationships focused on companionship rather than biological timelines. Partners can use relationship guides to navigate these conversations openly and honestly, ensuring both people understand each other’s expectations and goals.
Discretion improves with life experience
Franklin’s fourth reason highlighted practical wisdom: older women are “more prudent and discreet in conducting an Intrigue to prevent Suspicion.” He valued their ability to maintain privacy and handle delicate social situations with finesse. Their life experience taught them when to speak, when to remain silent, and how to navigate complex social dynamics without creating unnecessary drama or gossip.
This discretion extends far beyond romantic secrecy into general relationship management. Older partners typically understand the importance of maintaining boundaries with friends, family, and colleagues. They’re less likely to overshare personal details on social media or create awkward situations through poor judgment. Franklin noted that even if relationships became public knowledge, society would be more understanding of an older woman “who would kindly take care of a young Man, form his Manners by her good Counsels, and prevent his ruining his Health and Fortune among mercenary Prostitutes.”
Physical attraction remains surprisingly consistent
Franklin’s fifth point was his most provocative and detailed observation about physical intimacy. He noted that aging affects the body unevenly, with changes appearing first in the face and neck while “the lower Parts continuing to the last as plump as ever.” His famous analogy suggested that “covering all above with a Basket, and regarding only what is below the Girdle, it is impossible of two Women to know an old from a young one.”
Franklin added that “in the dark all Cats are grey,” meaning physical differences become less noticeable during intimate moments. He argued that experience could actually enhance physical relationships, noting that “every Knack being by Practice capable of Improvement.” While his language was dated, Franklin recognized that physical compatibility depends more on technique, comfort, and communication than purely on age. Modern couples often find that emotional connection and experience matter more than youthful appearance, especially when they invest in communication resources that help them express their needs and desires openly.
Moral consequences feel less severe
Franklin’s sixth reason addressed moral considerations: “the Sin is less.” In his religious and social context, he believed that intimate relationships outside marriage carried varying degrees of moral weight. He argued that “debauching a Virgin may be her Ruin, and make her for Life unhappy.” Franklin viewed relationships with experienced older women as less morally problematic because they weren’t corrupting innocence or potentially destroying someone’s future marriage prospects.
While modern society has evolved significantly in its attitudes toward relationships and personal autonomy, Franklin’s underlying concern about causing harm remains relevant. Older women typically enter relationships with clearer expectations and greater emotional resilience. They’re less likely to be devastated by casual relationships or to have unrealistic expectations about outcomes. This can create healthier dynamics where both people understand the relationship’s nature and boundaries. Partners who want to explore these topics further might benefit from modern relationship guides that address ethical considerations in contemporary dating.
Guilt and regret become minimal factors
Franklin’s seventh observation focused on emotional aftermath: “the Compunction is less.” He reasoned that “having made a young Girl miserable may give you frequent bitter Reflections; none of which can attend the making an old Woman happy.” This reflected his understanding that actions affecting vulnerable people create lasting guilt and regret, while relationships that bring joy to experienced individuals generate positive feelings instead.
This principle translates into modern relationship psychology. When people date others who are emotionally mature and enter relationships voluntarily with clear understanding, the potential for causing lasting harm decreases significantly. Older women often approach relationships from a position of strength rather than need, making interactions more balanced and mutually beneficial. They’re typically better at communicating their boundaries and expectations, reducing the likelihood of misunderstandings or hurt feelings. This creates relationships where both people can focus on enjoyment and connection rather than worrying about causing damage. Some people find relationship journals helpful for processing these complex emotional dynamics.
Gratitude becomes a defining characteristic
Franklin’s final and most emphatic point was simple but powerful: “They are so grateful!!” His use of double exclamation points suggests this was perhaps his most important observation. He noticed that older women appreciated attention, companionship, and romantic interest in ways that younger women might take for granted. This gratitude created positive feedback loops that enhanced the entire relationship dynamic.
Gratitude remains one of the strongest predictors of relationship satisfaction across all types of partnerships. When someone genuinely appreciates their partner’s presence, efforts, and attention, it creates an environment where both people feel valued and motivated to continue investing in the relationship. Older women, having potentially experienced loneliness, difficult relationships, or social invisibility, often bring deep appreciation to new connections. This can manifest in thoughtful gestures, verbal appreciation, and genuine enthusiasm for shared experiences. Couples who want to cultivate more gratitude might explore gratitude practices that help them recognize and express appreciation for each other more consistently.
Franklin still recommended marriage above all
Despite his detailed arguments about older women, Franklin concluded his letter by restating his primary advice: “But still I advise you to marry directly.” He viewed marriage as “the proper Remedy” for romantic longing and “the most natural State of Man.” Franklin believed that married life offered the best chance for “solid Happiness” and that postponing marriage for perceived advantages was misguided because those benefits were “not only uncertain, but they are small in comparison with that of the Thing itself.”
Franklin’s perspective on marriage reflected his belief that humans were meant to be partnerships: “It is the Man and Woman united that make the compleat human Being.” He argued that separation left each person incomplete, with men lacking “Softness, Sensibility and acute Discernment” while women missed “Force of Body and Strength of Reason.” This complementary view suggested that committed partnerships, whether marriages or long-term relationships, offered the greatest potential for personal fulfillment and practical success. Modern couples exploring commitment might find marriage preparation resources helpful for understanding the deeper benefits of long-term partnership that Franklin advocated.
Franklin’s advice reveals timeless insights about human nature, relationships, and what truly matters in romantic partnerships. While his language and social context were products of the 18th century, his observations about experience, character, discretion, and gratitude remain surprisingly relevant. Perhaps most importantly, his emphasis on marriage and committed partnership as the ultimate goal suggests that regardless of age preferences, lasting happiness comes from finding someone who complements and completes us.