Introduction: Gestational trophoblastic neoplasia (GTN) is a malignant form of gestational trophoblastic diseases originating from abnormal proliferation of placental trophoblasts. Owing to unusual and variable presentations, the diagnosis is sometimes delayed and become catastrophic. Though, survival outcomes are good following chemotherapy, but still surgery becomes first choice in hemodynamically unstable patient which is to be followed by chemotherapy depending upon the World Health Organization (WHO) prognostic score. The reproductive outcomes following chemotherapy is variable. Here, we are reporting a case series of GTN with varied presentation giving different lessons which were managed to best of our possible efforts. Case discussion: The first case highlights the management of women who had ruptured choriocarcinoma post manual vaginal examination for which hysterectomy was performed as a life-saving procedure followed by chemotherapy. The other case surprised the clinician with metastatic perforating invasive mole along with unusual finding of ovarian and iliac vein thrombosis. Although, planned for chemotherapy, hysterectomy with debulking was done for hemoperitoneum. The last case perplexed us with the normal twin conception just following the completion of chemotherapy for post-molar high-risk GTN and is continuing her viable pregnancy. Conclusion and clinical implication: Our case series imparted few lessons to obstetricians. Pelvic examination in GTN needs to be guarded so as to prevent untoward life-threatening complications. Invasive mole may present lately with devastating rupture uterus with exuberant pelvic vein thrombosis (PVT). Spontaneous conception with good reproductive outcome may still occur immediately following completion of multi-agent chemotherapy in high-risk GTN.