I've seen this question come up quite frequently and I've asked it myself as well: "What about multiple dialog entries?"
We're not talking about branching dialogs or having a complex dialog tree, however the current Talk-to and Popup-dialog aren't enough to simulate an actual conversation where the Player's Captain appears to actually talk to an NPC, something that I feel can help stimulate the Player's imagination by reinforcing the illusion that the Player is actually asking questions or making statements to the NPC rather than simply acknowledging one pop-up dialog after another.
Setting up multiple dialogs isn't supported by the Foundry tool set. The steps listed below however produce a simulation of a conversation between the player and an NPC contact:
To set up the conversation, you must hide multiple copies of interactive objects that the Player can interact with. I chose the Light Ray Small Effect object and placed 3 copies of it under the NPC.
After the objects are in place, you can use them in a [Complete All] mission goal so that each interaction appears together with all the other interactions as multiple entries in the Interaction Window.
Then, I laid out popup-dialogs for each interaction mission-goal, and that's it, basically.
The Player can then select to activate any of the interactions, which in turn trigger the popup dialogs as demonstrated by the set-up in this image.
That's basically it. It looks kind of ugly because the player is actually interacting with an invisible object, and this trick doesn't allow for a fluid conversation without a very involved set up, but it's a start, and I hope it helps.