Are you trying to imply the short sleeves instead of long, no winter hat with a pom pom, no cane using, non skinny as a rail gentleman on the left is Waldo from the Where's Waldo book series? Well I say this post is shit.
The iconic red and white horizontally striped shirt is reminiscent of Where's Waldo/Wally?
The books consist of illustrations depicting dozens or more people doing a variety of amusing things at a given location. Readers are challenged to find a character named Wally (or Waldo)
All this time we thought he was running and hiding but he wasn't running, nor hiding. He was searching and he finally found her. Waldina is the reason Waldo isn't hiding anymore.
My first thought was that this is around Belmont Park in San Diego, but that building on the left side of the picture has a bit of elevation, where the land around Belmont is flatter.