Smiling woman

Good morning, Foxkylefox!

Great attempt on such a hard angle of the face! The locations of the ears look very nice-- ears are very important to show how much a face is tilted and these look accurate :).

The back of the head/rest of the skull seems to be missing. There is quite a lot of room for the brain to sit, so make sure to include the back of the skull in your practice.

As for reducing stiffness, I think\ drawing contours is your biggest culprit preventing fluidity. Chicken scratch (making many short lines to create a longer line) erases the fluid qualities of a confident stroke. Try representing the face with structures it is made up of instead of the outlines. For example, the roundness of the cheeks, the planes of the forehead and nose bridge. The visible structure of the jaw curving underneath and the half-ball of mass on the chin. Studying facial structure (bones and muscles) and taking the time to sketch the shapes will allow you to represent complex forms into information for your gestures.

Another great exercise for fluid lines and no stiffness is trying continuous line drawing. You sketch without picking up your pen/pencil. It forces you to consider structure as you have to loop over the prior line you've already draw. It is the exact opposite of the game snake! Combining structure and contour results in really pretty effects.

Don't worry about your results at first! If it seems too daunting, draw a continuous line sketch without looking at your paper! You practice the skill AND you don't have to take the sketch seriously. I like to laugh at the sketches I make blind, but I can still appreciate the looseness of my linework.

Best of luck! Keep at it!

You're doing great! You're beginning to grasp the dynamics and anatomy of the human face, and I see where you're going. If you want to make the drawing more "smooth" and reduce the stiffness, I would suggest using maybe a softer pencil (looks like you're using HB or lighter), and try to make softer and longer strokes. Maybe even use circles and shapes to capture the essence of the face you're drawing. Using shapes will often kill the stiffness more.

Keep drawing!