Heteronyms are words with the same spelling, but different pronunciation/meaning. My friend and I were trying to come up with sentences that can be interpreted two different ways; here are a few of mine (italics on the heteronyms):

The President’s handwriting was sloppy on the treaty, so he resigned.

Hand me that sakazuki, for Christ’s sake!

The tailoring on my new shirt was terrible, so I stuffed it in the sewer.

Random

Wait, so, uh…should we cross? Everyone is shopping on this side.

Life, Random

My relatives were visiting this week, so I took the train out to the suburbs to see them. The next day they drove me back to Chicago, and during the car ride my aunt and uncle were discussing the difference between gregarious and loquacious.

I wish I could hang out with them all the time.

Life, Random