Q: "A curly-blond-haired man and a black woman wait to cross the street across from a photo store." Does this mean that "a man and woman both dressed in white wait to cross the street"?
A: it is not possible to tell

Q: "Two navy men and two young girls are playing monopoly." Does this mean that "people play monopoly"?
A: yes

Q: "Older gentleman writing with a pen on a desk." Does this mean that "The man is typing the letter on a computer."?
A: no

Q: "Man sitting with headphones at a laptop." Does this mean that "A man using headphones for privacy"?
A:
it is not possible to tell