What exactly is the right way to respond to a hand-crocheted portrait of a celebrity rendered with total sincerity? Or a piece of taxidermy assembled in a way that raises questions no one thought to prepare for? Or any of the hundreds of objects that Etsy’s handmade marketplace was quietly hosting in 2009, made with full earnestness by people who believed in them completely?
Regretsy, the blog that ran from October 2009 to January 2013, had an answer: post it on the internet with a brief, devastating caption. Whether that constitutes comedy, cruelty, or something more genuinely interesting has been worth thinking about ever since.
April Winchell, a voice actor and radio host who ran the site under the alias “Helen Killer,” launched Regretsy as a dedicated showcase for the strangest items listed on Etsy, the handmade goods marketplace that had launched in 2005 and become the largest independent craft platform in the world. Etsy by 2009 was hosting an enormous spectrum of earnestness: some of it beautiful, some of it strange, and some of it genuinely difficult to categorize.
Regretsy found the last category and put a spotlight on it. The site received nearly 90 million page views in its first four days. Random House offered a book deal within six months. The Los Angeles Times called it “wildly funny.”
The site’s tone was what made it work. Winchell was a writer with real comedic instincts, and the jokes tended to land on the absurdity of the objects rather than contempt for the people who made them. What Regretsy understood, almost accidentally, was that sincerity combined with genuine strangeness produces something that comedy almost can’t resist. The sellers featured on the site weren’t performing weirdness. They believed in what they were making. That gap between the maker’s seriousness and the reader’s reaction was where the humor lived, and navigating it without tipping into meanness required a specific kind of precision that Winchell mostly had.
In December 2011, Winchell organized a charity fundraiser through the site. Regretsy’s community had developed, by then, a reputation for collective action alongside its collective mockery. PayPal froze the fundraiser account, citing the use of a “donate” button, which the company said was restricted to registered nonprofits.
In the course of trying to resolve the situation, Winchell reported that a PayPal representative explained the policy this way: “You can use the donate button to raise money for a sick cat, but not poor people.” The line went viral. PayPal apologized publicly, reversed its decision, and made a donation of its own after Regretsy readers organized on Facebook and Twitter. The episode said something about what the site had quietly become: not just a comedy blog, but a community with a voice and a willingness to use it.
The pattern repeated. When the clothing retailer H&M used an independent artist’s work without permission or credit, Regretsy’s readers organized again. H&M initially apologized and promised to make amends, then quietly walked away from that promise. The second round of pressure produced a $3,000 donation to an animal shelter on the artist’s behalf. A blog that started by finding the most baffling listings on a craft marketplace had turned, in specific moments, into an ad hoc consumer advocate. Winchell would probably have resisted that description, but the record makes it difficult to avoid.
In January 2013, she posted a farewell. She had promised herself she’d walk away when the site stopped being fun. Winchell wrote: “After three and a half years, I’ve said everything I have to say about it, and now we’re just Bedazzling a dead horse.” She kept the archive online and preserved the forums, writing: “There is a wonderful, supportive community there, and I want those people to remain there and enjoy it for as long as they care to.” The site as a live, updating blog was finished. It had run for about three and a half years.
What Regretsy caught was a specific moment in two things at once: internet culture and craft culture. Etsy itself has changed considerably since 2009. It’s now a platform where professional sellers operate at scale, where algorithms surface bestsellers, where the handmade aesthetic has become a commercial category with its own conventions and expectations. The kind of edge-case earnestness that Regretsy thrived on has either been pushed to the margins or found its own audience through short video platforms, where sincerity and strangeness have become legible entertainment formats in their own right. Regretsy found those objects funny partly because the internet in 2009 wasn’t used to rewarding that kind of unguarded earnestness. That has genuinely changed.
What I find interesting, looking back at Regretsy, is that the best of it wasn’t purely a joke at someone else’s expense. It was something more like appreciation through mockery, or mockery through appreciation, depending on the post. There’s something I genuinely respect about a person who makes an unusual object with full commitment and offers it to the world without apparent self-consciousness. There’s also something irresistibly funny about it. Regretsy didn’t resolve that tension. It lived in it, and produced most of its best work right at the intersection of the two. That’s a harder balance to maintain than it sounds, and the fact that Winchell knew when she’d exhausted it, and said so cleanly, is as good an ending as that kind of site could have had.
