And lastly, the ultimate two subject composition ...

Hmm, Mike,
 

I feel sort of like I resemble the blonde in the last painting today..LOL.

I have spent lots of time with these two men, however, it was probably 15 years ago, so Alex is all grown up now, but the father I know fairly well. The wife wants it casual and I picture them in button downs and jeans, possibly the father in a chair..club or wing maybe and Alex sitting on the arm that would bring them really close together with them being touchy feely like the mothers and daughters in the other two portraits. Does that sound ok?

Mary,

Two subject composition is tough duty. I would try and give some variation in either head height, depth (front/back), body language etc. See if you can find another element like the arm of the chair or maybe a background lamp to play up and balance the overall composition. Michele did this very effectively just recently (using a lamp in 2 person composition.) Maybe one of those free-standing slender lamp stands about five feet tall. The son to our left, the father seated with legs crossed oriented toward the son, and the lamp to our right with the shade half way between their heads in height.

Personally, for men I don't think a close touchy pose is in order. The fact that these two men appear in the same frame suggests more than a little emotional closeness.

One more thought, often times body language can be suggestive of the "relaxed and casual" look. A man can look totally relaxed and at ease, even formally dressed, depending on body language.

You might try doodling on paper with just the big shapes.

I'm tapped out from here, I'll pass the baton.

The pose where one sits in a chair, and the other stands behind the chair with a hand resting on it is nice. A wingback is good for a formal look. I can't imagine why a person with his background would want to be portrayed in jeans, but hey, I just have a bias againt jeans I suppose.

They could also both stand, one facing you, one facing 45 degrees another way, with his head turned toward you.

When I did a portrait of a couple I talked with them for a while, to get a sense of their personalities. The woman was the more outgoing, while the man was happy, supportive, and kind. This told me all I needed to know about how to pose them, and what expressions to encourage. What are these guys like?

Another great one is nude Greek wrestling. Just how casual can you get?