1635 W Irving Park Rd
Built from an ancient railroad dining car with one counter and zero tables, this 24hr eatery is a perfect, no-nonsense old-school diner -- and one of the best in all of Chicago. See if you can stomach the legendary Slinger -- a giant pile of eggs, hash browns, chili, grilled onions, and burger patties with cheese -- or opt for the off-menu Dick Burger, complete with a runny egg and hash browns.
2945 N Broadway
A great li'l wine and cheese bar with a huge emphasis on the cheese part, Bar Pastoral is the bistro outpost of one of the multiple cheese-shop only locations. Take your date to the winter prix-fixe dinner of raclette -- a Swiss dish of melted cheese paired with potatoes and charcuterie -- just maybe not the first date, as dairy is quite gaseous. Just looking out for you.