High-school friend Ray was the second portraiture-practice session I did while visiting my folks over the new-year break, the first having been a family friend. I like the results from the first session, but I didn't like that I was still so awkward/skill-less on how to conduct, on a person-to-person level, the portraiture session. Technical skill with the camera accounts for maybe 10% of what's needed... the rest is all in how you interact with the person.
Shoving a lens in someone's face and saying “smile” may work fine if the someone is a professional model, but it sure makes normal people feel awkward, something not conducive to photogenic results.
This time I had an epiphany: even if I feel awkward/skill-less on how to do it, pretend I know exactly what I'm doing. The confidence-building effect on the subject should be the same.
So, I went over to Ray's house and talked a bit about taking a picture, surveyed the living room for a good angle, then set up a silly shot to break the ice:

Nikon D4 + Voigtländer 125mm f/2.5 — 1/320 sec, f/4, ISO 6400 — image data
Deep Thoughts
contemplating life's mysteries with Bloom County
But after that I moved into stealth mode, just chatting about work/life/kids/etc while I snapped pictures, more or less omitting the whole photo thing from the conversation except for the occasional “look this way” or the like.
So not only did I get to catch up with an old friend, during the normal course of conversation I got all kinds of looks for the camera (mostly laughs), and he seemed to become more comfortable. Then at the end we could try some specific looks.
It was a different experience with his wife, Jill. I pointed the camera at her, she flipped a switch that turned on a beaming fashion-model, and I took, literally, two frames, and we were done.
I missed focus on this frame of the pair (I need to not forget about the “10% technical skill part”!), but one can sort of hide that with a bit of “funky joy” negative clarity in Lightroom, something you can really do with a guy's portrait.

Nikon D4 + Nikkor 85mm f/1.4 — 1/320 sec, f/1.4, ISO 1800 — image data
Square
version of the lead photo
as might be useful for an online avatar
Nice catch lights in the eyes. What lighting arrangement did you use?
Setting him in a chair in the middle of a room that had a large window to camera right. —Jeffrey
I don’t know if you’ve already seen this, but Strobist had a wonderful series of articles on portraiture last year by master portrait photographer Sara Lando. I found them fascinating, and they’ve definitely changed the way I think about shooting portraits. The first one can be found here: http://www.strobist.blogspot.com/2012/08/on-photographing-people-pt-1.html.
Maybe that’ll help with the mental aspect of it.
Yes, I saw those when they came out… well worth a read! —Jeffrey
Bloom County – perfect! Great photos.