Q: "A man with sunglasses on top of his head is playing a slot machine." Does this mean that "A man with sunglasses on top of his head is gambling at the slot machine"?
A: yes

Q: "A group of people walking, within the group is a lady wearing a shirt that says Bliss." Does this mean that "A group of people walking to their next class."?
A: it is not possible to tell

Q: "A boat with a roof on green water." Does this mean that "The water is filled with bears"?
A: no

Q: "a girl wearing pink hangs on the hoops." Does this mean that "A girl hanging."?
A:
yes