(1) Background: Postoperative pain is a frequently underestimated complication significantly influencing surgical outcome and patient satisfaction. While abdominoplasty is one of the most commonly performed plastic surgery procedures, studies investigating postoperative pain are limited in current literature. (2) Methods: In this prospective study, 55 subjects who underwent horizontal abdominoplasty were included. Pain assessment was performed by using the standardized questionnaire of the Benchmark Quality Assurance in Postoperative Pain Management (QUIPS). Surgical, process and outcome parameters were then used for subgroup analysis. (3) Results: We found a significantly decreased minimal pain level in patients with high resection weight compared to the low resection weight group (p = 0.01 *). Additionally, Spearman correlation shows significant negative correlation between resection weight and the parameter “Minimal pain since surgery” (rs = −0.332; p = 0.013). Furthermore, average mood is impaired in the low weight resection group, indicating a statistical tendency (p = 0.06 and a Χ2 = 3.56). We found statistically significant higher maximum reported pain scores (rs = 0.271; p = 0.045) in elderly patients. Patients with shorter surgery showed a statistically significant (Χ2 = 4.61, p = 0.03) increased claim for painkillers. Moreover, “mood impairment after surgery” shows a dramatic trend to be enhanced in the group with shorter OP duration (Χ2 = 3.56, p = 0.06). (4) Conclusions: While QUIPS has proven to be a useful tool for the evaluation of postoperative pain therapy after abdominoplasty, only continuous re-evaluation of pain therapy is a prerequisite for constant improvement of postoperative pain management and may be the first approach to develop a procedure-specific pain guideline for abdominoplasty. Despite a high satisfaction score, we detected a subpopulation with inadequate pain management in elderly patients, patients with low resection weight and a short duration of surgery.