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I'm very happy with how this one came out, especially the background. It just suddenly popped into my head, 'why not make it a nautical theme?'
I put the dog in front to break up the boring area in the woman's dress. The guy standing next to her is afraid of dogs. The guy next to him smoking a cigar is holding out a sausage for the dog.

I wanted to give a lot of depth and 3-dimensionality to this picture, so I put a guy with a pool cue on the right. He's just messing with the guy in the foreground, tapping him on the shoulder. I also put a woman's foreshortened arm above the cynophobic (afraid of dogs) man.
The guy ringing the bell in the background is yelling "Come and get it!"
Under the archway on the left, I put two crossdressers. A guy is pointing a gun at one (although it's hard to tell). He really hates crossdressers. There's also one in the left middle-ground, holding a beer mug.

The woman on the left foreground is looking at a man proposing to a woman (it ties in to the 1810's one). She's saying 'awwww, how sweet.'. Her boyfriend is trying to talk and is saying "Honey, are you listening to me?" She's going to turn around and smack him and say "Why don't YOU do something sweet like that?"
The guy in the foreground to the right of them is suffering from a migrane.
The bird on the bar (on the right) is called a curlew sandpiper.