OH no! i'm making a dropdown menu!!

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Well, then I would take the 2nd example, and change the \itemkind field into a string. The string can be used to classify items, so you can determine for each item in the typelist, to which (sub)list it belongs. Sort of like this:
;itemlist type
Type itemlist
  Field name$        ;name of the item
  Field belongs_to$  ;to determine to which list the item belongs
End Type

;create two items for list called 'list one'
item.itemlist = New itemlist
item\name$ = "New"
item\belongs_to$ = "list one"

item.itemlist = New itemlist
item\name$ = "Load"
item\belongs_to$ = "list one"

;create two items for list called 'list two'
item.itemlist = New itemlist
item\name$ = "Dave"
item\belongs_to$ = "list two"

item.itemlist = New itemlist
item\name$ = "Dan"
item\belongs_to$ = "list two"

;print stuff that belongs to list one
For item.itemlist = Each itemlist
	If item\belongs_to$ = "list one" Then Print item\name$
Next

WaitKey()
End