Originally Posted by macropod

What you're asking for simply isn't possible with Word. If you want something to appear in a Table of Contents, that 'something' must be part of the same paragraph as the entry itself. Style separators can't be used for that, either. If your paragraph numbers are in a different paragraph from the heading, they'll at best appear as a separate entry in the Table of Contents. The obvious solution is to apply a suitable numbering scheme to the headings themselves.