Giant ovarian cysts, which are described in the literature as measuring more than 10 cms in size in their largest diameter, are rare in occurrence. With the availability of multiple imaging modalities and routine physical examinations, it has become even rarer to find such cases. Ovarian serous cystadenomas, which are benign tumors arising from the ovarian epithelium, represent the most common type. We present a case of a 58-year-old female who came to establish primary care in our clinic. She reported ongoing symptoms of constipation, abdominal discomfort, bloating, as well as intermittent postmenopausal bleeding for the past few months. The patient reported taking over-the-counter medications for her predominant gastrointestinal symptoms with no improvement at all. Transvaginal ultrasonography (TVUS) and magnetic resonance imaging (MRI) of the pelvis revealed the presence of giant bilateral ovarian masses measuring more than 17 X 10cms each. Further testing revealed highly elevated levels of tumor markers cancer antigen 125 (CA-125) and human epididymis protein 4 (HE-4). The patient subsequently underwent total abdominal hysterectomy (TAH) and bilateral salpingo-oophorectomy (BSO). Her histopathology report revealed the presence of bilateral benign cystadenomas. From a primary care physician's perspective, this case highlights the importance of possible rare pathologies that can present with symptoms of a completely unrelated organ system. Even with the rarity of these cases, a clinician may encounter such a case in their everyday practice. Patients can endorse a plethora of vague complaints, often masquerading other entities seen commonly in the clinic.