Neighborhood: Near North Side
Address435 N. Clark St. 

Three Dots And a Dash is a tiki themed bar without the cheesy, bamboo-ridden tastelessness of a Jimmy Buffet concert parking lot. This joint has an endearing novelty that makes transitioning between conversation topics easy, which is an absolute luxury during a first date. Like, if you get caught up in a 25-minute-long soliloquy about her CrossFit WOD or how her cat "totally sits on the couch like a person," you can point out the bar's smoldering, punch-filled treasure chests and say, "Whoa, those are cool. Right?" Then, you can interject with a breakdown of your fantasy football team. Just joking. Ask her about her job or whatever.

As an added bonus, this place is sandwiched between Bub City and Paris Club, which are perfectly worthwhile places to keep a good date going, or—if things aren't going so hot—ideal spots to salvage what remains of your Saturday night.