Wednesday, August 05, 2026
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Last week, a tweet about a nuance of dating in the app era unleashed an avalanche of reactions online. It even ignited a clash inside Esquire. The reporter Alyson Krueger talked to single people to find out what they think of the Great Uber Debate. You can read it below. –Michael Sebastian, Editor-in-Chief
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The president is selling Wall Street early access to his brain farts, and in return you get diarrhea from a salad.
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As if planning a first date weren’t stressful enough, a new expectation for guys has emerged: sending their date an Uber to pick them up. Oh, and it better be an Uber Black! “It’s very weird not to send a car,” declared Madison Campbell, on the social-media platform X, when talking about what she wants for a first date.
Her July 30 post, in which she also said that “every good man I’ve ever been on a date with has sent a car (usually a black one),” became an instant Rorschach test for dating in the app era. Some screamed that demanding such treatment was an immediate red flag, proof that the woman is too entitled. Or, if a dude suggests it, he’s clearly a serial killer in waiting; do you really want a stranger knowing where you live and tracking you?
The Great Uber Debate has roiled the straight dating scene at precisely the time when taking a woman out is already an expensive endeavor. What it reveals is the growing divide across America in which some women don’t even want a guy to open a door for them while others embrace the trad-wife trend, opting for complete subservience to their man.
I know, if you’re a single guy, it’s all very confusing. What is the protocol here—has it suddenly become table stakes to send your date an Uber Black to take her to dinner?
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For a year or so in my twenties, I had the pleasure of working at an outdoors store in Chicago. The store was called Uncle Dan’s and it was basically a local version of an REI. The time I spent working at Uncle Dan’s made me an expert in outdoor gear. I can tell you why Osprey makes a better backpack than Deuter and recite from memory the specs of an Arc’teryx outer shell. I even know what Gore-Tex is and how it works. But none of that compares to the amount of useless information I have about water bottles.
But ask me which brands made the best water bottle, and I’d be hard-pressed to answer, because they all had issues. The Hydro Flasks leaked; the Yetis were too heavy; the straw on the Camelbak was impossible to clean; and the Nalgenes, though adorable, were impossible to drink from. What I learned from the year I spent hawking water bottles is that there’s no such thing as a perfect water bottle. At least there didn’t use to be. Enter the Owala Free Sip.
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If you’re looking for someone to thank for the timeless allure of the safari jacket, you could do a whole lot worse than Ernest Hemingway. America’s long-running one-man adventure story almost single-handedly propelled Africa—or a literary version of it—into the public consciousness in America when he published Green Hills of Africa in 1935. And along with it came the gear. For Hemingway, being knowledgeably equipped was an integral part of the man-of-action persona he carefully cultivated. He ordered his provisions—multi-pocketed safari jacket among them—from leading American outfitters like Willis & Geiger and Abercrombie & Fitch, having them tweaked and adapted to suit his exacting needs.
As functional clothing goes, the safari jacket, albeit without the life-threatening experiences, still has a functional charm about it that is perfectly attuned to the rigors of modern summer travel. What makes it so adaptable is its weight. It’s often referred to as a jacket, but given its lightweight construction—usually in cotton or linen—it’s actually somewhere between a shirt and a jacket. Historically it was often worn with short or rolled sleeves for added comfort. Military origins mean that specific details—including a fitted waist, four pleated pockets, a shirt-style collar (so it could be worn over bare skin), epaulets, and a belt in matching cloth—differentiate it, if you’re a purist, from other functional pieces, like the now ubiquitous chore jacket.
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