ChapelR's Dialog Macro internally uses SugarCube's Dialog API to show it's dialog, and as I understand things due to how that API is implemented only a single Dialog can be shown at a time.
This can be demostrated using the following example with will result in only the 2nd of the two dialogs being shown.
<<link "Open Two Dialogs?">>
<<script>>
Dialog.setup();
Dialog.wiki("Contents of Dialog 1");
Dialog.open();
Dialog.setup("Character Sheet");
Dialog.wiki("Contents of Dialog 2");
Dialog.open();
<</script>>
<</link>>
You could use the above behaviour to chain a series of dialogs, and the following shows one very basic way to do that using ChapelR's macro..
<<link 'Talk to Robot'>>
<<set _option to "">>
<<dialog 'Player'>>\
You talk to the robot.
<<link "What is 2 + 2?">>
<<set _option to "1">>
<<dialog 'Claire'>>\
"Beep! 2 plus 2 is four."
<</dialog>>
<</link>>
<<link "What is 3 + 3?">>
<<set _option to "2">>
<<dialog 'Player'>>\
"Beep! 3 plus 3 is six."
<</dialog>>
<</link>>
<</dialog>>
<</link>>