This essay uses a literary device to create a transcript of an imagined con
versation between postmodern philosophers Ludwig Wittgenstein and Jean-Fran
cois Lyotard with two family therapy trainees, Jack and Jill, in order to e
xplain key postmodern concepts as they might relate to family therapy. Thes
e include Lyotard's concepts of a differend, paralogy, meta-narrative, and
Wittgenstein's concepts of a language game, language game confusions and fa
mily resemblance. Other postmodern theorists and therapists make cameo appe
arances in the conversation, tying their own ideas to the topics under disc
ussion. The essay also addresses the criticism of postmodernism raised by B
arbara Held.