Some time around March, Sam let me know that she’d like me to paint her portrait for her birthday (in May).  The first step was to pick the right photo.  After a few photoshoots and hundreds of shots we chose this photo to work from:

The painting was to be done on cradled masonite, which I’d never painted on before.  I started with a basic wash of where everything should go and then set out to create the “background.”

Something is not quite right about the face in this wash – but I’ll work on that later.  First I tried several times to figure out what the background would be.  I first thought some kind of flowery amorphous fuzzy thing, in pink to match the dress she would be wearing.

Okay, maybe not.  Although it looks “okay” up in the top left it just doesn’t seem to bring anything to the piece.

I tried going orange.  Don’t ask why – because I don’t know.

Frustrated with the background I decided to work on the actual body first and worry about the background later.

Looking at the piece though – something doesn’t seem right about the face.  I took tracing paper to the photo and laid it over the painting to make corrections:

Still not an exact likeness – but better than before.  I like hands, so I did a lot of work on the hand before eventually getting back to the background.  I decided to put her on a park bench so we could see a more lively background.  I thought this would work since she was resting her arm on the back of the chair.

Painting wood is hard.  I still haven’t figured out how to do it without looking “cartoony.”  Next came some trees.

I decided to make them cherry trees to bring in the pink accents again from what would eventually be her dress.

But how do you convincingly make millions of little flowers in the distance?  Not easy – and I didn’t really accomplish it, but this is the extent of my skills at the present time.

And so from here I worked on the dress, the skin more and finally the hair – to end up here:

It looks a little very “cartoonish” – but at least in a consistent way.  The teeth are really white, aren’t they?  I kept trying to take them down a bit – but then I’d always put more white on, because how could I give this to her with anything but sparkly white teeth?