As you see, I drew the mermaid above the water and the horseback rider on the shore. Easy solution, but what about horseback riding and a beauty queen?
In this case, I couldn't rely on the picture being outdoors, where I could just place the figures anywhere, so I put the beauty queen on the stage and the horseback rider on the floor with the audience. Instead of cluttering up the scene with word balloons, I let the viewer come up with the narrative. In this case, the gentleman surmised that he was sweeping the beauty queen off her feet after her victory. It became their story, not mine, though they appreciated the part I played.
There are a number of occasions when I've drawn as many as five faces and bodies on a live caricature. I'll dig around and see if I can find the pics I took of them.