Stef and the City

Stef and the City is a Chicago-based dating service that provides personalized matchmaking and dating coaching to help singles find long-term relationships. They assign a dedicated recruiter who vets, screens, and interviews every potential match, offering an affordable alternative to traditional intro services by focusing on quality connections. In addition to matchmaking, they offer services such as personalized social calendars, events, and singles travel to broaden opportunities for clients.

AI named Stef and the City from December 2025 to September 2026.