Ridiculous History (iHeartPodcasts)

Episode: CLASSIC: Benjamin Franklin's Advice On "Finding A Mistress"
Air date: November 22, 2025
Hosts: Ben Bowlin (A), Noel Brown (B)

Episode Overview

This episode dives into the bizarre, scandalous, and surprisingly well-documented sex life of Benjamin Franklin, focusing especially on his infamous 1745 letter, "Advice to a Young Man on the Choice of a Mistress." The hosts explore Franklin’s reputation as a womanizer, the content and tone of his advice, and the blurred lines between genuine counsel and sly satire. The episode also discusses Franklin’s broader persona—his myth, achievements, human flaws—and the tension between his public ideals and private conduct.

Key Themes and Discussion Points

Franklin: Renaissance Man or Libertine? (00:00–04:36)

• Hosts set the stage: Franklin is introduced as an eccentric founding father, scientist, publisher, diplomat—and notorious womanizer.
• Franklin’s physical appearance and charisma are discussed; despite not being conventionally attractive, his wit and influence made him popular with women.
• "He was lionized for this because people said, you know, old Ben is a real pickup artist for his day." —Ben (00:49)
• The show acknowledges Franklin’s flair for the pleasures of the flesh, joking about whether “he would’ve been in the Epstein files.”
• Brief mention of Franklin’s daily routine, "air baths," and legendary “paunch.” (07:25)

Unpacking the 1745 Letter: Satire or Sincerity? (04:36–23:16)

• Franklin’s actual words are read:
  "Marriage is the proper remedy. It is the most natural state of man and therefore the state in which you are most likely to find solid happiness." —Franklin, quoted by Ben (04:36)
• The hosts discuss whether the letter, which gives advice on how to select a mistress, was sincere or satirical.
• Definition of “mistress” at the time clarified: a sexual partner outside of marriage, by today’s understanding. (02:09)
• Franklin’s own admissions about his affairs from his autobiography are recounted, including this censored quote:
  “The hard to be governed passion of my youth had hurried me frequently into intrigues with low women...which were attended with some expense and great inconvenience, besides a continual risk to my health by distemper.” —Franklin, paraphrased by Noel (10:23)
• Franklin allegedly fathered up to 15 illegitimate children. Hosts point out his conduct would be "a Me Too nightmare" today. (11:34)
• Discussion of Franklin’s dubious relationships, possibly spanning mother and daughter simultaneously.
• Paradoxical: While known for dalliances with young women, Franklin in this letter extols the virtues of older lovers for practical and, he claims, ethical reasons.

Franklin’s 7 Reasons for Preferring Older Mistresses (13:36–21:12)

The hosts summarize Franklin’s arguments:

1. Conversation is better: Older women are more interesting and experienced.
2. Gratitude and devotion: He claims they will be more appreciative.
3. Discretion: Less likely to cause social scandals.
4. No risk of children: Less chance of unwanted pregnancies.
5. Preservation of allure: “In the dark, all cats are gray.” Physical differences are less noticeable.
6. Less sin: Claimed as less immoral than seducing virgins.
7. Diminished regret: Fewer moral repercussions; allegedly makes older women happy.

Memorable (cringeworthy) quote:
“The face first grows lank and wrinkled, then the neck, then the breast and arms, then the lower parts continuing to the last, as plump as ever. So 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 one from a young one. And as in the dark all cats are grey…” —Franklin, quoted by Ben (20:13)

The hosts dissect the misogyny and self-serving logic in Franklin’s writing, noting the letter was never actually sent and is widely believed to be sincere despite its outrageousness.

Was Franklin Joking?

• “This doesn't seem funny enough to be satire.” —Producer Casey Pegram (29:03)
• Consensus: despite Franklin’s reputation as a satirist (e.g., writing Fart Proudly), this letter seems largely earnest.

The Myth and Reality of Franklin (23:16–27:33)

• The hosts reflect on the way Franklin's mythic status has whitewashed his less savory behaviors.
• "It is crucially, crucially important for us to acknowledge that this person was a human being and not just some airbrushed ideal of early America." —Ben (24:25)
• Biographers (e.g., Albert Henry Smith) have described Franklin’s sexual behavior as “deplorable errata” and marked by “irredeemable vulgarity.”
• Franklin’s hypocrisy, particularly writing about virtue while practicing otherwise, is highlighted.

Other Odd Franklin Pursuits (27:06–28:50)

• Brief tour of Franklin's other eccentricities:
  • Fart Proudly (a satirical essay)
  • Rumored membership in the hedonistic Hellfire Club
  • Glass harmonica invention—hosts play and describe its spooky sound (28:08)
  • Prior episode on Franklin’s attempt to make a new alphabet

The 200+ Drunkenness Euphemisms (33:05–37:25)

• The hosts return to a fan-favorite Franklin creation: his comically extensive list of synonyms for being drunk.
• Perform a reading, relishing the absurd variety (“thump over the head with Samson's jawbone,” “cat chagrined,” “non compost,” “nymphtopsical”).
• "I feel like most of these work really well if you say them in a cockney accent." —Noel (33:29)
• Discussion about whether Franklin collected these sayings from pubs or invented them himself.

Listener Mail (37:25–40:19)

• Entertaining letters from parents about innovative tooth fairy traditions, including notes from “fairies in drug rehab” and “the Lost Teeth Chronicles.”

Notable Quotes & Timestamps

• On Franklin’s reputation:
  "He was also a real lothario, a crazed womanizer, a sex fiend." —Ben (08:31)
• On Franklin’s advice to his friend:
  “In all your amours, you should prefer old women to young ones. You call this a paradox and demand my reasons…” —Franklin, read by Ben (13:36)
• On the darker side:
  "If he was around today, this guy would be a Me Too nightmare." —Noel (11:34)
• On morality:
  “It's less sinful to sleep with an old woman than the act of, quote, debauching of a vir.” —Noel (22:34)
• Reflecting on Franklin’s complexity:
  "...not just some airbrushed ideal of early America. Which, not to say that he didn't do some amazing things, it's just that he did a lot of horrible things." —Ben (24:25)

Segment Timestamps

• 00:00 — Introducing Franklin, the lecherous founding father
• 04:36 — Reading and unpacking Franklin's letter on choosing a mistress
• 10:23 — Franklin’s autobiography confessions and his legendary libido
• 13:36 — The seven "reasons" for preferring older mistresses
• 20:13 — "In the dark, all cats are grey" and Franklinian misogyny
• 23:16 — Sincerity vs. satire; reflections on Franklin’s morality
• 27:06 — Franklin’s quirky inventions, including the glass harmonica
• 33:05 — Readings from Franklin’s 200+ synonyms for being drunk
• 37:25 — Listener mail: Tooth fairy creativity
• 40:53 — Closing banter, invites for listener submissions

Takeaways

• Benjamin Franklin was not just a statesman and inventor, but also a deeply flawed and at times unsavory individual, especially in terms of his private life.
• The 1745 letter is a window into Enlightenment-era sexual ethics—by no means modern or progressive, and certainly rife with misogyny.
• While Franklin remains an American icon, the hosts argue for grappling honestly with the darker facts about his character.
• The episode’s tone is irreverent but thoughtful, balancing humor about Franklin’s excesses with serious reminders that history’s heroes were (and are) human.

For Further Reading / Listening

• Advice to a Young Man on the Choice of a Mistress (full text available online)
• Franklin’s list: “The Drinker’s Dictionary”
• Earlier Ridiculous History episodes on Franklin’s inventions and pranks

Summary prepared for listeners seeking a lively, unvarnished look at the private vices, public mythmaking, and genuine eccentricity of one of America’s strangest founders.