This paper argues that not only in his first novel, The Sun Also Rises (1926) but also in the posthumously published work, The Garden of Eden (1986), characters have harnessed a shameful reaction to life—they are at the same time adamant about pursuing their interests and desirous of retreat with the slightest setback, embarrassed about the unrequited emotional investment and unable to completely relinquish their aroused interest or joy. Lost in the loops of affective positivity and negativity, the individuals in Hemingway are caught in the ups and downs and the passes and returns of the sensations of shame. Together the two novels that nearly bookend his career as a committed and compassionate prose writer capture the shame in and of modernity—the shamed action of and is life, with all its strivings.