Comments just on the new one.. the focus is on the hands, not the eye, but it's not far off. You don't need to shoot everything at f1.8 just 'cos you can.
The fact there is no light from the right is not a problem, it give the image depth and direction. The light on his face is actually very nice.
The background is a problem though. You're finding out that to
create (rather than
take) a portrait you need to take control of your environment - as well as taking the camera out of auto you need to move yourself, move your subject and control the light. A diffuser from the middle of a 5-in-1 reflector is useful for creating open shade when you have no other choice but then unless you are close and have a diffuser you can use one handed* you'll need an assistant or a reflector holder + stand (and sandbags, tentpegs, bungee cords, etc). And all that stuff needs to be instinctive so you can concentrate on interacting with your subject.
I recommend practising on a teddy.
*This is the only one I can think of that actually works well one handed:
http://www.lastolite.com/product_list/1066861.85450.1067079.0.0/TriGrip_Difflector