They say men's biggest fear is being laughed at, so it's a good thing these men are dead. Dating History takes the world’s most famous (and famously dead) men—from emperors to inventors—and runs them through the ultimate modern dating test. With sharp humor and a healthy dose of gossip, the hosts weigh their charm, quirks, and dealbreakers to decide: would they be relationship material today?
LBJ: More of a Drake or a Kendrick? With the help of special guest Prance, Analisa and Katie address this and other questions while discussing the legacy of the man who created PBS and NPR while simultaneously escalating the war in Vietnam — simply because he didn't want to look dumb.
6 Dec 2025
I Never Would've Dated... Ernest Hemingway
In this episode, Katie and Analisa, alongside their esteemed guest Caroline Timoney, break down Mr. Macho Man Ernest Hemingway, a man known for his concise, restrained prose — because only men can make an accomplishment out of using less words. You'd think that a writer famous for being a Man of Few Words wouldn't be such a mansplainer, but alas. Topics include: his four marriages, his penchant for bullfighting (again?!), and a hearty discussion on whether or not tires are overpriced.
9 Nov 2025
I Never Would've Dated... Napoleon Bonaparte
This episode is a little bit about Napoleon and a lot about scabies. Haven't heard of it since you were in AP USH or went through that obsessive historical fiction phase in 5th grade? Well you're in luck for a refresher when Dating History welcomes its first ever podcast guest, the inimitable Kylie Brakeman!!
24 Oct 2025
I Never Would've Dated... Johnny Cash
Johnny Cash was avoidant; Reese Witherspoon is perfect. Analisa and Katie talk about Johnny Cash and whether or not Joaquin Phoenix should be allowed to make any more biopics.
9 Oct 2025
I Never Would've Dated... Pablo Picasso
If you've ever had a man's mother warn you against dating him, this episode is for you. Analisa and Katie tackle a serial cheater with a penchant for age gap relationships, and discusses how people stay in relationships with narcissists. The conversation veers toward Woody Allen, Analisa makes a bunch of impressive literary references, and the word "squalor" is said an unreasonable number of times.
26 Sept 2025
I Never Would've Dated... JFK
There once was a time when America was led by a young, charismatic and, dare we say, undeniably hot, former senator from Boston. Some call him the 35th president, we call him a Gemini who couldn't keep it in his pants. Analisa and Katie yearn for the idea of having a hot and cool president, and discuss the Marilyn-Jackie paradox.
11 Sept 2025
I Never Would've Dated... Albert Einstein
In this week's episode, we start with the theory of relativity, and arrive at our own theory — that men with sisters respond faster. Analisa discusses Einstein's obvious similarities to Justin Bieber, and we go in-depth on the trend of important men treating their wives as secretaries.
28 Aug 2025
I Never Would've Dated... Ben Franklin
Ben Franklin... known to the world as an inventor, but to us as a Capricorn with unmedicated ADHD. We begin the episode discussing how he never actually married his wife then move on to Analisa's Four Boyfriend Theory, who Benny F. would have been today, and the horror of being asked "What are you thinking about?" on a date.
14 Aug 2025
I Never Would've Dated... Henry David Thoreau
Analisa and Katie's discuss the life and loves of the one and only Henry David Thoreau, leading them into a discussion about van life guys, death anxiety and male hair loss.
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