Painful sexual intercourse is one of the earliest known female sexual dysfunctions and has a complex clinical profile requiring a multidisciplinary approach. This disorder, on the pathophysiology of which many studies have been reported, has also been defined as an expression of somatization. Disrupted emotional awareness, called alexithymia, which is strongly associated with somatization, may have a deleterious effect on treatment response. This chapter is a selective review of the science on genitopelvic pain/penetration disorder (GPPPD) and alexithymia. It focuses on two separate but related topics. It begins with the debates on the definition of GPPPD from past to present and what multidisciplinary approaches have suggested. It then continues with the definition of alexithymia, its neural correlates, and its relationship with psychiatric disorders. Finally, it informs us about the direction of future studies by pointing out where GPPPD and alexithymia meet.