How about we… put Klondike Bars and Guinness Stout in a blender and enjoy our beer milkshakes.

• Drink - bar

How about we… discuss whether we're really sad that summer's almost over, or really happy that fall's almost here.

• Other
• a coffee shop

How about we… play tennis, see a subtitled art house movie, & eat lobster -- a la Annie Hall. http://bit.ly/anniehalldate

• Play
• all over

How about we… find a deli that makes a killer "Thanksgiving leftover" sandwich.

• Eat

How about we… celebrate National Taco Day by tracking down the best Taco Truck in the city and trying all the tacos on their menu. http://bit.ly/nrX5Jm

• Eat

How about we… go shopping for new school supplies (even if neither one of us is going back to school).

• Shop
• an office supply store

How about we… skip straight to dessert and go on a macaron crawl.

• Eat

How about we… find a bar with great margaritas and unlimited chips & salsa.

• Drink - bar

How about we… take a free dance lesson and then test our new moves in the park at Chicago SummerDance?

• Play

How about we… go to a park, swap iPods, and try to identify each other's music with our eyes closed.

• Other