Gestational trophoblastic diseases (GTD) comprise a heterogeneous group of disorders arising from genetic anomalies occurring during fertilization in twin pregnancies and often may be associated with assisted reproductive techniques. An exceedingly rare presentation of GTD is a twin pregnancy hydatidiform mole with a co-existing fetus, condition which may be an important cause of complications for the mother and the fetus. A 36-year-old woman (G2, P0, A1) underwent a friendly controlled ovarian stimulation (COS) followed by intrauterine insemination (IUI) for assisted reproductive purposes, resulting in a twin pregnancy initially characterized by two gestational sacs. However, one sac failed to progress and instead degenerated into molar trophoblastic disease, while the other sustained a normal fetus with regular growth. At 33 weeks gestation, the patient developed preeclampsia, necessitating delivery via cesarean section at a tertiary care facility. Reproductive-assisted procedures may be linked to cases of trophoblastic disease. Additionally, the presence of cystic lesions warrants a wide differential diagnosis, with magnetic resonance imaging serving as a valuable tool for accurate assessment and differentiation of structures.