Hilarity and Heartbreak

‎"I want that which is hilarious and that which is heartbreaking to occupy the same territory in my writing because I think they very often occupy the same territory in life, much as we try to separate them." ~ Richard Russo

Can hearts really break?  Where do the pieces go?  Do hearts even wrinkle?  

Why don't your toes ache when you suffer emotional pain? 

Add hilarity and mix the two.  Can you approach the territory Russo desires?