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

How about we… take ballroom dancing lessons at Access Dance.

How about we… do a progressive dinner - appetizers, entrees and dessert each at a different place.

How about we… hunt for the perfect ice cream sandwich. http://bit.ly/mxW55Y.

How about we… write down a bunch of random questions, put them in a hat and get to know each other by pulling them out, one at a time.

How about we… go to trivia night at a local bar and see who gets the most questions right.

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

How about we… find a place where we can crack open a lobster. Bibs optional.

How about we… buy the craziest hats we can find and walk around town ignoring the stares.

How about we… test our Boy Scout skills and try to start a bonfire without a match. Then we can make s'mores.

How about we… celebrate our Irishness (real or pretend) and create our own St. Patrick's Day bar crawl.

How about we… buy some cheap umbrellas & hand them out to people caught in a downpour.

How about we… do something outdoors, then play paintball, then grab a bite -- a la 10 Things I Hate About You.

How about we… celebrate the U.S. Open by playing a round of mini-golf? (It's JUST as prestigious.)

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

How about we… grab gourmet Belgian beers and frites at The Publick House.

How about we… check out an art gallery neither of us has visited before.

How about we… play tourist and go take pictures of the best holiday decorations around town.

How about we… give poutine a try...then take a long walk to try to undo the damage to our arteries.

How about we… say 'to heck with Cannes' and go on a sneaky, tipsy, movie-hopping date of our own. http://bit.ly/jaCUQH.

How about we… buy some cheap umbrellas & hand them out to people caught in a downpour.

How about we… break all the dating rules -- eat with our hands, be cheap, and be competitive. http://bit.ly/fQiMXF

How about we… go to a beginner's class of a language we both want to learn.

How about we… rent a convertible for the day and drive around with the top down.

How about we… get our sangria on before the fall's fully here.

How about we… spend the day at the Aquarium? It's like the zoo, but with air conditioning.

How about we… see who's better at paintball.

How about we… grab a pillow and swing at each other during International Pillow Fight Day. Maybe grab a bite after if we're not coughing up too many feathers.

How about we… check out how our favorite animals are keeping cool at the zoo.

How about we… someone to talk and have dinner with.