Something I’ve found is possible is several “routes.”
There would be one route in which the hero talks to Henry, and gets a token indicating he’s done that. In the second route, the hero lacks the token.
If the hero has the token when talking to the second mate, the second mate would walk off to the side.
If the hero lacks the token, he is teleported to where he fights the second mate.
It takes some fancy coding footwork, but I’m sure you could do it! ^u^ If you need an example, Falling Glory uses this route framework in Thaba.
Sorry if this is late, and good luck!