Are you new to comedy podcasts, overwhelmed by the array of options, and wondering where to begin? Then welcome to “Start Here,” a recurring guide to the best comedy podcasts available — and our recommendations for which episodes are the best entry points to your next auditory obsession.
It can be hard to laugh about money, particularly if you, like most of us, have little of it. But this is precisely what makes Gaby Dunn’s Bad With Money podcast feel downright magical. Dunn, a multi-hyphenate comedian-writer-filmmaker, has hosted BWM since its inception in August 2016, shepherding it through various changes to its format and network (after stints on Panoply and iHeart, it is currently produced by the Cumulus Podcast Network). In early seasons, the show focused primarily on its host’s personal financial problems — overspending, student loans, retirement planning — and their attempts to rectify them by speaking with family members and celebrity friends. Later, it morphed into a space for Dunn to couch unusually vulnerable conversations with financial experts like Suze Orman or journalists like The New Yorker’s Jane Mayer inside episodes centered around more global fiscal concerns, such as the real-world costs of an abortion, workers’ strikes for fairer wages, and the argument for reparations.
Across every incarnation (and often within the same episode), Dunn regularly reiterates what a grim situation it is for most people: Disparities in wealth are expanding rapidly in the United States, the one percent continue to get richer at the expense of everyone else, and the system is fully and completely fucked. But Bad With Money is hardly apocalyptic programming. Unlike those podcast hosts dedicated to enriching your bank account before the end-times, Dunn seems to want to help listeners comprehend that in a world actively trying to drain, rob, or even kill them, they are not alone in being financially illiterate. Every recording runs on hypercuriosity and a radical buoyancy far more familiar to fans of Just Between Us, their comedy-variety podcast with longtime business partner Allison Raskin, than to regular finance podcast subscribers. When an interview is skewing too dour, Dunn slyly lifts it with generous, commiserating giggles until both host and guest are cracking up at the shittiness of it all. It is, to cite the cliché, the kind of show that often makes you laugh through your tears.
That mix of raw vulnerability, substantive financial advice, and pure dumb jokes is never more potent than in “The Sexy, Sexy Sex Episode,” the
horniest seventh episode of season eight from August 18, 2021. As Dunn puts it in the opening monologue, “This episode is so far from a bummer, it almost feels like too much of a treat, like an indulgence.” The episode opens with a major announcement: Dunn is officially nonbinary and their pronouns are they/them/theirs, as evidenced by the sparkler they held in their coming-out photo. Appropriately, says Dunn, this “very queer” episode will dive deep into the costs of an active sex life over two segments: a look at dating with Autostraddle’s Wait, Is This a Date? co-hosts Drew Gregory and Christina Tucker, and a cards-on-the-table discussion about sex with Boyslut author Zachary Zane.
But first, the host issues a warning: “This is not an episode for the faint of heart. Seriously, if you listen with your grandma, now may not be the time, unless your grandma has some thoughts on how not to overspend trying to get pounded, ya feel?”
Five minutes in, the dating segment begins innocently enough. When Dunn questions how they handle their money while dating, Gregory (“who I have also kissed,” Dunn admits) and Tucker (“who I have not kissed, but you never know”) suggest that the secret to keeping costs reasonable is keeping the emotional stakes low. For example, says Gregory, there is no need to buy a new outfit for every date. And, Tucker chimes in, a strong date can be as simple as meeting on a nice patch of grass somewhere, especially if you’re queer: “It’s very gay. We are going to have a picnic by some waterfront park. That’s what we do, as a people.”
But what about dating when you are completely broke, asks the host. Surely that’s an insurmountable challenge? Not so, says Tucker: “I did my best dating when I was broke. Though now that I think back on it, I was broke dating cis men, and it was easier for me to say, ‘Now you pay. Now. Your money.’” Gregory agrees, then adds that laying bare one’s brokeness on a date might even help to establish a playful power dynamic. “If you have a certain identity or energy you’re trying to get across, payment can become a part of that,” she says. “Like, I’m expecting this other person to pick up the tab, and I’m gonna be cutesy about it, that’s a certain energy.” “It’s bottom energy,” razzes Tucker. “Just call it what it is.”
The segment closes after 26 minutes with Dunn, Tucker, and Gregory riffing on the weight of such factors as generational wealth, debt, and income inequality between queer partners. For Dunn, the subject is personal: They make a higher income than their partner but don’t have that partner’s familial wealth, which creates tension around rent and other baggage. Unsurprisingly, it’s just as loaded a topic for their guests. Gregory sums up her own concerns this way: “I don’t think my boss realizes what it takes as a trans woman — even one who isn’t super-high femme — to get ready to go in the morning. If I’m going on a date, multiply that by whatever. Being trans means that there’s more hair to remove.”
The next segment moves into bawdier territory as soon as Dunn introduces Zane as a sex expert they met “at a bisexuality conference hosted by the Obama White House, if you can believe that is a sentence.” Appropriately, their first topic is the cost of sex parties, which Zane discusses with the aplomb of the well experienced. They’re generally not cheap (around $60 to $80, he calculates, depending on the amenities) and often exhausting enough that they require calling an Uber instead of walking home at 4 a.m.. Thankfully, gay get-togethers tend to be more affordable than straight ones, says Zane with a laugh: “Ya go in, ya get pounded, ya bust a nut, and ya leave within 15 minutes.”
“So what has been the biggest waste of money you’ve had in pursuit of sex?” Dunn asks. “Everything!” Zane jokes.
But in reality, he admits, going to certain parties where the dynamics around consent are looser than elsewhere can be both upsetting and expensive. Better to cut your losses, even if you bought tickets two weeks ago and still haven’t had a chance to “stick it in” than suffer some kind of violation or trauma. “You don’t have to be there!” Zane advises. “You’re a grown-ass man/woman/nonbinary cutie, and you can just … leave.”
As they did in Bad With Money’s very first episode, Dunn wraps this one by asking Zane a most challenging question: How do you pay the rent? Zane responds with rare glee at the fact that he makes a living by celebrating his great love of fucking, even if it can sometimes be a hustle to bring home the bacon. “Writing pays shit,” he warns (preacher, meet choir), which is why he’s pivoted into a part-time brand ambassador known for his “swipe up to not get erectile dysfunction” posts. But when push comes to shove, “you can always write SEO content like ‘what are anal beads?’ and shit it out,” he says. “Pun intended, baby!” Dunn shouts.
With such a fun note as its ending, it is hard not to recall how rare conversations so frank and funny still were when this episode aired. Truthfully, they still are. But Dunn creates such solidarity with their guests that it feels possible for us, too, to have 45 minutes of unbridled talk about money, sex, and dating without defaulting to shame or depression. It’s just too bad no grandmas will ever know that.
More From This Series
- Want to Try I Said No Gifts!? Start Here.
- Want to Try Don’t Ask Tig? Start Here.
- Want to Try Random Order? Start Here.