Whenever I can, I like to draw pictures of my favorite subject: My beautiful wife, Leanna. I drew this one tonight while she laid in bed thumbing through pictures of Joe Rocket motorcycle jackets on her smart phone (not shown).

This was drawn free-hand and without any measurements. I like that I am getting more confident about drawing that way. I’ve learned a few tricks for being able to do that while observing a live subject:

• Start with overall shapes and angles. I started this drawing with a diagonal line from the top right to bottom left that followed the general flow of her face from her eyebrow to her chin. I build everything else off of that line.
• Focus on the angles of the subject in relation to imaginary verticle and horizontal line. My first attempt at this initial line, not shown, was too shallow. Other lines, the line of the bottom of her nose, the angle of the eyse, and the direction of the crease between her lips were all compared with imaginary horizontal and vertical lines.
• Compare positions of elements both vertically and horizontally as you go. Draw a vertical line from the tip of her nose and you’ll see it just misses the corder of the mouth. A vertical line from her left eye goes directly past her earlobe. By comparing positions of elements both vertically and horizontally, you don’t have to measure in order to get correct proportions. Trigonometry will make sure that elements are the right size and distance from each other.
• Notice where one feature crosses over another. The nose crosses over the far cheek. The lips cut above the line from the cheek to the jaw. The bridge of the nose cuts in front of and contains the far eye. These are key points for giving your drawing the appearance of three dimensions. 
• When drawing the edge of a three-dimensional feature, give it three sides. The top lip goes up on its leftmost edge (1), to the right and down across its top edge (2), and then has a slightly more acute angle continuing to the right and more steeply down.

Once I had the facial features done, I worked on adding hair. I liked the way her hair framed the edge of her face as she lay on the pillow, so I used the natural darkenss of her hair to bring out the edge of her face rather than relying on a simple line. This also gives the picture a more natural, three-dimensional feel. Lines don’t exist in the real world, only edges where two different elements meet.

Does she look like she is sleeping or looking down? The key distinction, and the only real indication in this drawing is the little, light crescent below her left eye. That is the edge of her lower eyelid. It is a small thing, but that is how we know if an eye is open. In an open eye, the edge of the lower lid catches more light.

I drew the picture with an HB pencil. I took the picture with my iPad. The light wasn’t great, so I touched up the  color and exposure in Photoshop Touch.