I'm just really getting into it now but ideally some fast glass helps. I focus on the eye and shoot at around f/5 (gives a nice soft background bokeh but keeps their face sharp - usually) but make sure your shutter speed is up around 1/250 or higher as they wont hold still for long usually
If moving then you'll need 1/500 (again ideally) to capture the movements
Ideally if he'll sit for a few shots, maybe shoot on Av and do a few shots of the same setup with different apertures to see what works best for your lens (or the 'sweet spot' as it's often called). Also I advise shooting RAW so you can recover in PP or just bring a small amount of sharpening or clarity into the shot.
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