This essay offers a reading of Henry James's Portrait of a Lady that examines Isabel Archer's choices through a Lacanian lens. This reading traces Isabel's consistent turning away from, even against, the very postulates she claims to live by. Isabel’s discovery of love through the ideal image of herself she ﬁnds mirrored in Gilbert Osmond’s gaze leads to a reversal of her most noble impulses. Her choice of a suitor also points to something that would seem the opposite of desire, but which is, in fact, its foundation. In choosing Gilbert Osmond, Isabel seeks to experience, however unconsciously, what Jacques Lacan deﬁnes as jouissance, or “painful pleasure."