Originally Posted by
GrumpyDiver
Welcome to the world of portraiture. First learning - glasses are a pain to shoot, so having the subject remove them is usually the best plan. They tend to do a few things that you don't want; reflections (as is the case in your shot) and the distortion of anything behind them. They can also cast shadows that can be distracting; if you look at your subjects eyes, they have what I refer to as "goofy shadows", cast by the subjects lenses and frames. If the glasses are part of the personal of the person being photographed, removing them from frames is sometimes done. Speaking of distracting, the white spot behind your subject that is camera left is definitely a bit distracting.
Depending on what you are trying to do with the image, there are two major directions in portraiture lighting. One is what you see in commercial headshots, where the lighting is very flat and even, then the objective is to have a shadowless image. If the shot is a more traditional portrait, then shadows to accentuate specific facial features or looks are used. In this shot you have a fairly noticeable dropoff as the top of the head has significantly more light than the bottom. I don't thing that is necessarily working for you.
I do like the way your subject's eyes are natural (not too open and not too closed), that gives a much more "comfortable" look.
I find your crop is a touch too close for my taste (looks too much in the ID card / passport style). Leaving a bit more clothing in often works better compositionally than getting too close.
You suggest that you need a second flash; I'd agree that a second light would help, but that doesn't necessarily mean you need a flash; I often use a reflector as my fill light. A decent sized piece of white foam core or coreplast is a lot less expensive than a second lighting setup. Collapsible commercial reflectors area my preferred choice; and while they come in different shades and colours, most of my portraiture is done with a white reflector. If you are shooting men, a silver reflector can make the lighting look a bit "edgier". The nice thing about a reflector is that you don't need to worry about lighting ratios; reflected light tends to not overpower your main light source.
A good place to start with your main light is the 45 / 45 position; flash either camera left or camera right 45° from the camera plane, pointing down at your subject at a 45° angle. The reflector or second flash should be positioned so that it comes in from lower down and points up a bit to fill in things for you.
As for a shooting angle, you'll have to play around with that a bit. My usual "safe" choice is to be a touch about higher (an inch or two) than eye level.