Ask Jeeves launched in 1996 as the search engine where you could literally type your question in plain English—no Boolean operators, no “+” signs, just “What’s the weather in New York?” and it would try to answer. It used natural language processing before that was even a buzzword, and had its mascot, Jeeves, a butler who “fetched” your answers. In 2001, they rolled out Teoma as their core search technology, which gave more relevant results, and over the next few years they kept tweaking the engine. But by the mid-2000s, Google’s speed and accuracy left Ask Jeeves in the dust. In 2006, the butler got retired, the site rebranded as Ask.com, and the quirky Q&A vibe faded. For a lot of us, though, Ask Jeeves was the first time a search engine felt like you were talking to a person instead of a machine.