Q: "a man wearing a yellow shirt with a dramatic look on his face" Does this mean that "The man is dramatic looking."?
A: yes

Q: "Two young adults are working on a chalkboard." Does this mean that "A young man and woman are working on a chalkboard."?
A: it is not possible to tell

Q: "Man attempting to fix something." Does this mean that "A man fixes something."?
A: yes

Q: "Dog swimming in the water with a stick." Does this mean that "A dog is outside in the pool"?
A:
it is not possible to tell