Increasingly it seems that analysts and their patients are in the midlife period. If analyst and patient are both going through a midlife crisis involving similar issues, this may have repercussions in the analysis. Turning to the literature for guidance reveals a paucity of papers concerning the clinical application of midlife developmental theory. This article explores such an application by describing the effect of two midlife changes—time urgency and role reversal with respect to aging parents—on the transference- countertransference in the analyses of two middle-aged patients.