Noticed these two laughing in the sunshine. Here's my take on what's going on. They know each other, work together; they're waiting for the door to open so that they can report to work. She rode to work on mass transit, her entire commute. He rode most of the way on mass transit, then changed to his skateboard for the rest of the way.
This second photo shows the two of them still laughing and obviously still waiting on that door.
The door now open, the lady's already stepped out of sight except for a corner of her purse. He's holding it open for her and, from the shape of his cheek, is still smiling. I believe these two had a great day at work! Since they're entering an unmarked door, I'd be guessing where they work, but at the time I took this photo, I think the downtown Nike store was still in the building to the left of the door. He's wearing Nike shoes. I can't see the sides of her shoes, but I believe there's a swoosh on her jacket. So, I'm thinking they worked in the Nike store in the multi-story building known as the Public Service Building, designed by prolific Portland architect A. E. Doyle, completed in 1927.