1. He is watching something on his phone but he also needs to have an eye on his son behind him.
He needs a way to be watchful of his son and listen to whatever he's listening to. Also, he needs something to stay awake in the early morning train rides.
2. He is listening to music on his way to the Giants Game. He also is battling against morning drowsiness.
He needs a way to wear his sunglasses, listen to music, and stay cool all at the same time.
3. He is listening to music and trying to keep himself awake.
He needs something to stay awake.
4. He is a skateboarder who likes to listen to music. He seems tired at the moment.
He needs a way to listen to music and ride his skateboard simultaneously.
5. He is on his way to San Francisco and listening to music.
He needs a way to keep himself not bored.