The one rule: when she says something, respond with content before any question — an assumption, interpretation, opinion, tease, story, callback, or playful exaggeration. Interviews score zero. Attraction lives in the guess.
Who are you talking to?
M Marisol, 28 mural painter · Pilsen D Danielle, 31 ER nurse at Illinois Masonic · Bridgeport P Priya, 24 marketing analyst, DePaul grad · Lincoln Park C Camille, 34 jazz singer, books tables at a restaurant · Uptown J Jess, 26 barista, improv student at Second City · Wicker Park E Elena, 29 7th grade science teacher · Little Village S Sofia, 33 architect, marathon runner · Lakeshore East T Tasha, 30 music publicist · West Loop I Ingrid, 36 owns a small bakery · Andersonville G Grace, 25 medical student at UChicago · Hyde Park Where?
Coffee shop, Logan Square
Bar, River North
House party, Pilsen
Art gallery, West Loop
Brown line platform
Street fest, summer
How into talking is she?
Cold
She's not looking to talk. Win her over.
Neutral
Polite but unimpressed. Your move.
Warm
She's chatting happily. Don't fumble it.
Start the conversation