Resolution
 

How do I run the game in a 16:9 aspect so everything isn't 'squished'.

Common resolutions for 16:9 are 640×360, 854×480, 960×540, 1024×576, 1280×720, 1366×768, 1600×900, 1920×1080

DW doesn't allow widescreen resolutions (16:9). And at best it allows 800x600, 1024x768, 1280x1024, so 4:3 and 5:4 only.

Alternatively you may be able to let your videocard driver settings to scale the game resolution to your screen resolution. But make sure you make it maintain the aspect-ratio, or circles will look like ovals, and squares like rectangles. There will be black bands on the side of the screen though, a neccessary limitation.

And setting your screen resolution to 16 bit colordepth allows to enable windowed mode.