"Joe’s is a good choice when you’re interested in potentially moving this person into first or second-tier territory. It’s a nice wine bar in the West Loop, and the Italian small plates are really good—plus, you’re probably going to be sharing things. If you need to wait for seats, do a little team-building activity and strategize about what to order. We like the fried artichoke, parmesan puffs, and ricotta gnudi with confit pork cheek." - adrian kane