Objectives: The art of esthetic dermatology has reached its pinnacles in this generation providing treatments for almost all skin concerns. Throughout history a myriad of issues have risen, and one that is common to everyone is the pigmentation of their intimate areas. Many people, particularly women, lament that their dark underarm makes it impossible for them to wear their favorite sleeveless dress or that they must deal with their partner’s embarrassment due to this issue. Even though cosmetics have advanced and we now have answers for every issue, people are still hesitant to undergo these treatments, even though they want to get rid of these pigmentations. This study has multiple goals, it aims to determine the reasons behind people’s reluctance to undergo depigmentation procedures in intimate areas, the extent to which dermatology has advanced in society, and whether skincare is still taboo. Material and Methods: Using an online survey through Google Forms, we conducted a cross-sectional study dated from May 21, 2023, to July 05, 2023, collecting data from 112 people living in Tbilisi, Georgia. Most of the participants were in the 18–35 age range. Participants responded to 17 questions about their overall skincare routines, the amount of time and effort they put into skincare, and their thoughts on the depigmentation process in private areas. Results: From a total of 112 participants, 69.6% (n = 78) were female, and 30.4% (n = 34) were male, with the majority of participants from age group 18 to 24 [83% (n = 93)], followed by people who are 25–30 [16.1% (n = 18)], and 2% from age 31 to 40 [0.9% (n = 1)]. In that, 62.5% (n = 70) of the population was interested in receiving treatment, but they were hesitant for a variety of reasons where 47.3% (n = 53) reasoned the high cost. About 8.9% (n = 10) were also reluctant to expose their intimate areas during procedures. About 8.9% (n = 10) of people think that they are intrusive and refuse to have them done. About 2.7% (n = 3) refuse to get the treatment due to opposition from spouses and family. Varying opinions about skincare approaches were also recorded where 33% (n = 37) stated that they have never been to a dermatologist since they have not experienced any skin problems whereas 21.4% (n = 24) use homemade skin care products, whose efficacies are debatable. Conclusion: Our investigation emphasizes the blending of medical and cosmetic components of dermatology by demonstrating positive responses regarding depigmentation and dermatologic procedures. A greater demand for solutions to skin pigmentation problems in sensitive areas of the body is reflected in the growing popularity of intimate area depigmentation. Nonetheless, the choice to receive these treatments is kept private and is shaped by cultural conventions, society expectations, and individual preferences. Some desire depigmentation for greater comfort and confidence while others value natural beauty and self-acceptance. The two biggest obstacles to involvement are lack of information and financial limitations. To combat this, easily accessible skincare solutions that have been shown to work should be reasonably priced and come with easy-to-follow directions that will allay worries and promote making wise decisions.