This is my answer to your challenge, Time out for art thanks Lisa Zeebra.
He looks sad but he is full of mischief. I just lack the talent to make him look happy. Maybe trying to get him to stay still made him sad. If he would have just sat still I think I could have put a smile on his face. I was tempted to put a cartoon smile on his face but that is not the challenge, a cartoon smile is too easy.
I got him to stay still by eating a biscuit and he sat there looking so mournful. You would think he was starving, dogs make you guilty every mouthful you take with their pleading look.
This drawing reminds me of a poem I knew as a child. ‘A loan wee waif of tawny brown. Adrift in the roar of a headless town. That begs as plain as tongue can sue. “Oh mister please may I follow you.” ‘I do not know who wrote it or any more lines. Maybe some one can jog my memory?