The car-buying business has changed a lot since — one of the internet’s first classified car ads websites — debuted in 1998, but the Chicago-based automotive marketplace is getting with the times. Today it announced a new matchmaking experience that uses AI to help car buyers find the ride of their dreams.

“We’re treating people like human beings with distinct emotional nuances, not just site users, as we build a more relevant, personalized car shopping experience,” chief product officer Tony Zolla said in a statement. “Early-stage car shoppers don’t know what they’re looking for. In fact, an overwhelming majority are undecided on make and model, yet nearly all online car search experiences force people to select make or model as the first step in their journey.”

The new search feature — built on the back of’s 5 million car listings and 6 million editorial, user, and professional car and car dealership reviews — is aimed at the more than 70 percent of shoppers who haven’t yet decided on a make and model. Leveraging sentiment analysis and natural language processing, it offers a guided, algorithmic approach to recommendations, surfacing cars likely to appeal to individual sensibilities.

Here’s how it works: Rather than having users specify a car brand or series,’s search tool instructs them to enter a price range, must-have features, and roughly a dozen “lifestyle preferences.” (Categories include “family taxi,” “daily commuter,” “fun and play companion,” or “workhorse.”) Then it presents them with a Tinder-like…