Hey @andydayton
take a look at this
https://github.com/roymacdonald/DLibTest
The tricky part with DLib is to add the correct includes. But once you figure it out it is very straight forwards.
In this example we are not opening new windows, although it might complain if you dont have xQuartz installed.
Let me know how it goes.
BTW, I just started an addon for using DLib inside OF projects, inspired in the way that ofxCV deals with different data types, wrappers, etc. I should be pushing it to github anytime soon.
Best