What’s the right way to respond to a hand-touched portrait of a celebrity taken in all honesty? Or a piece of taxidermy assembled in a way that raises questions no one thought to make? Or any of the hundreds of objects that Etsy’s handmade marketplace quietly hosted in 2009, made in all seriousness by people who absolutely believed in them?
SorryThe blog, which ran from October 2009 to January 2013, had the answer: post it online with a short, devastating title. Whether it was comedy, cruelty, or something more interesting has been worth pondering ever since.
Voice actor and radio host April Winchell, who runs the site under the pseudonym “Helen Killer,” launched Regretsy as a dedicated showcase for the weirdest items listed on Etsy, the handmade goods marketplace that launched in 2005 and has grown into the world’s largest independent crafting platform. Until 2009, Etsy was home to a huge spectrum of seriousness: some cool, some weird, some really hard to categorize.
Unfortunately, he found the latter category and focused on it. The site received nearly 90 million page views in the first four days. Random House offered a book deal within six months. The Los Angeles Times called it “wildly funny”.
The tone of the site turned it on. Winchell was a writer with real comedic instincts, and the jokes relied on the absurdity of the objects rather than disdain for the people who created them. What Regretsi understands, almost by accident, is that sincerity combined with genuine weirdness makes comedy almost irresistible. The sellers listed on the site did not exhibit any quirks. They believed in what they were doing. The space between the creator’s seriousness and the reader’s reaction was where the humor lived, and navigating it without turning it into sleaze required a special precision that Winchell possessed more than anything else.
In December 2011, Winchell organized a charity fund through the site. The community of regrets had by then acquired a reputation for collective action as well as collective irony. PayPal froze the fundraising account, citing the use of the “donate” button, which the company said was limited to registered nonprofits.
While trying to resolve the situation, Winchel informed A PayPal representative explained the policy this way: “You can use the donate button to raise money for a sick cat, but not for poor people.” The line went viral. PayPal apologized to the public, reversed its decision, and made its own donation after Regretsy readers organized it on Facebook and Twitter. The episode said something about what the site has quietly become: not just a comedy blog, but a community with a voice and a willingness to use it.
The pattern was repeated. When clothing retailer H&M used an independent artist’s work without permission or credit, Regretsy’s readers organized again. H&M first apologized and promised to make amends, then quietly backtracked. In the second round of pressure, $3,000 was donated to an animal shelter on behalf of the artist. A blog that began with finding the most confusing listings in a craft market has at certain moments evolved into a dedicated consumer advocate. Winchell would probably resist this description, but the note makes it hard to resist.
In January 2013, he released a farewell post. He promised himself that he would walk away when the site stopped being fun. Winchell wrote: “After three and a half years I have said all I have to say about it, and now we are just flogging a dead horse.” He kept the archive online and maintained the forums, writing: “There’s a wonderful, supportive community there, and I want those people to stay there and enjoy it as long as they care.” The site was completed as a live, updating blog. It worked for about three and a half years.
What Regretsi captured was a special moment in two things at once: internet culture and craft culture. Etsy itself has changed a lot since 2009. It is now a platform where professional sellers operate at scale, where algorithms uncover bestsellers, where the handmade aesthetic has become a commercial category with its own conventions and expectations. The serious seriousness that Regretsi developed was either sidelined or found an audience through short video platforms, where sincerity and weirdness became readable entertainment formats in their own right. Unfortunately, he found these objects funny in part because the internet in 2009 wasn’t used to rewarding such unguarded seriousness. It has really changed.
What’s interesting to me in retrospect is that the best part of it wasn’t just a joke at someone else’s expense. It was more like scornful appreciation or mockery through appreciation, depending on the post. There is something I really respect about a person who makes an extraordinary object with complete commitment and presents it to the world without apparent self-awareness. There is also something irresistibly funny about it. Unfortunately, he could not overcome this tension. He lived there and created most of his best work right at the intersection of the two. Maintaining that balance is harder than it looks, and Winchell knowing when he’s running out and saying so cleanly is about as good an ending as a site like this can get.
