Q: "This young girl smiles while she wears a wreathe of flowers in her hair." Does this mean that "The young girl is wearing a large hat."?
A: no

Q: "A man playing with a small dog." Does this mean that "A man is near a small dog."?
A: yes

Q: "A man fishing while standing on a small boat holding a net" Does this mean that "An elderly man is fishing."?
A: it is not possible to tell

Q: "Three young men are playing around while playing Monopoly at a table." Does this mean that "Three guys playing monopoly."?
A:
yes