More Die of Heartbreak (1987), Bellow's eleventh novel, recaptures much of the old Bellow energy and comedy, but falls short of both the intellectual scope of Herzog or the metaphysical and cultural explorations of Humboldt's Gift. It illuminates the tragicomic manner in which heterosexual relationships have failed in the late twentieth century. It is a Prufrockian lament about failed men and absent mermaids. Full of misogynous love-lore, comic characters, botched loves, fatal forays into the danger zones of sex and romance, farcical retreats, and serio-crackpot sexual philosophizing, this text provides the analogue of Bellow's end-of-the-century comic despair over the impasse of heterosexual relations. Misogynous in its narrative construction, it is the self-ironic report of two men exchanging stories of battle wounds with each other and an implied reader or narratee. The exchange functions at the expense of women whom they perceive to have failed their romantic expectations, because it stages only the scopophiliac male gaze, enacts binary, sterotypical gender ideologies, and sympathetically exonerates misogynist men. Clearly its intended audience is a certain kind of male reader. The center of consciousness in the text is Kenneth Trachtenberg, a self-appointed guardian and guide for the eccentric plant morphologist, Uncle Benn Crader, whom he perceives to be one of the rare, visionary men of the age. As Uncle Benn's erotic needs assert themselves and he becomes embroiled in modern marriage, family scheming, fraud, legal battles, and betrayal, Kenneth panics and attempts to rescue him. Like the works of Bellow's middle period, More Die of Heartbreak is another examination of the damage modern life inflicts on men of sensibility. 

Bellow's schedule of gender complaints in this novel is lengthy: the triple failure of science, religion, and belle lettre to illuminate love, modern distortions in human relations, the meaning of sadomasochism, the interconnection between love and death, the failure of modern marriage, the ironies of biological sexuality, the contemporary failure of poetry in human relations, and the comic incompatibility of heterosexual love with the male quest for higher consciousness. The mode of the novel is very much that of the Gogolian farce, "The Bridegroom," with its classic misogynous tale of the flight of the bridegroom from entrapment in marriage. The upshot of the marital failures of Kenneth and Benn is that both protagonists turn viciously on women for their collective failure to accept, arouse, anticipate, love, minister, or compensate them perfectly enough. On the plane to Tokyo, the occasion of Benn's second bridegroom flight, Kenneth eagerly advances his project to deconstruct "Woman" for his uncle. He explains that Benn's superior spiritual nature attracts educated women who are affected by these emanations, and who otherwise live in metaphysical darkness. It is a characterization of women as parasitic, metaphysically deficient, and in need of "fixing." It is also a deliberate attempt to reconstruct the celibate male enterprise by the familiar Bellow exclusion of the female erotic. Benn is last seen hightailing it for the Arctic wastes and his beloved lichens, while Kenneth settles for a woman who, perceiving his preference for flawless, classical female beauty, has had her lumpy face sanded by a dermatologist in order to attract him. It is a book that is no doubt extremely clever and funny to one set of readers and more than a little disconcerting to another. Reviewers were mixed in their response to it and there is, as yet, no consensus of critical opinion as to where it ranks in the Bellow canon. The final impression left by the novel is its portrayal of men as unfortunate sexual victims of droll and mordant mortality full of contaminating women who are metaphysically devoid of value. Sex and women appear to be cruelly funny jokes played on men who, without such handicaps, would appear in their true colors as noble, chivalric, and spiritually enlightened. Its preferred solutions are celibacy and bachelorhood, preserved if necessary by deception, abandonment, or flight.