Q: "A boy talks on his cellphone, while riding a horse through an event." Does this mean that "A boy talking to his mother on his cellphone"?
A: it is not possible to tell

Q: "A baby smiles while sitting next to a holiday display." Does this mean that "A sitting baby is seen smiling"?
A: yes

Q: "Man in a kayak swimming in rough waters." Does this mean that "A man is in a kayak during a dreary day."?
A: it is not possible to tell

Q: "Person with blond flyaway hair playing guitar" Does this mean that "Someone is playing music."?
A:
yes