Background: Nutcracker Syndrome is a rare anatomic reduction of the aorto-mesenteric angle (<22°) and distance (<8mm), causing flow congestion and significant pain. It is more commonly symptomatic in 20-40-year-old females, concerning for obstetric consequences due to prolonged pelvic congestion syndrome, anemia, and chronic pain. Methods: This single-center retrospective cohort study included 73 female patients who underwent surgical repair for NCS between 2019 and 2025. Statistical comparisons were made using chi-squared and t-tests (significance threshold p < 0.05). Binomial and multivariate logistic regression were performed using Jamovi version 2.6.26 to calculate odds ratios (OR). Results: Non-parous patients more often had gastroparesis (p=0.003), POTS (p=0.00004), EDS (p=0.003), mast cell activation syndrome (p=0.0009), and abdominal pain (p=0.005). Parous women more commonly experienced pelvic congestion and heaviness (p=0.003, 0.0007), leg swelling (p=0.005), and varicose veins (p=0.020). Parous patients used more opioids pre-operatively (33.3% vs 13.5%, p=0.031) and no difference was seen post-operatively (50.0% vs 48.6%). Pelvic congestion syndrome prior to surgery predicts symptom resolution (p=0.019, OR=3.9). History of childbirth (OR=4.7) and concurrent antidepressant use (OR=8.4) were independently associated with pre-operative opioid use. Conclusions: Parous and non-parous women with NCS present with distinct pain profiles, likely influenced by lasting hemodynamic changes of pregnancy and differences in comorbid conditions. Increased use of opioids by parous patients pre-operatively could be contributed to higher rates of pelvic congestion syndrome and misattributed pain blamed on postpartum and gynecologic causes, portending a longer time to diagnosis. Understanding differences in presentation and likelihood of opioid use is critical, as NCS is rare and prompt recognition is imperative to addressing chronic pain to improve quality of life.