Unexplained infertility (UEI) and advanced maternal age (AMA) provide considerable obstacles to reproductive treatment. Unexplained infertility is a diagnosis of exclusion; nonetheless, therapies like intrauterine insemination (IUI) and in vitro fertilization (IVF) can enhance outcomes. Age-related infertility is mainly caused by decreased oocyte number and quality and increased aneuploidy rate. The decline in fertility associated with ageing is predominantly permanent, highlighting the necessity of early intervention and fertility preservation. There are crossroads between these two entities. We should know where the cliff is so we can intervene early before the prognosis becomes poor. Expectant management and intrauterine insemination are viable initial approaches for younger women; maternal age necessitates a shift toward ovarian reserve assessment and prognosis-based interventions. Preimplantation genetic testing for aneuploidy (PGT-A) may enhance reproductive success, though it remains debated due to cost and variable efficacy. The outcomes of assisted reproductive techniques (ART) decline significantly beyond the age of 40, with live birth rates becoming negligible after 44. A strategic, individualized approach balancing natural conception, fertility preservation, and assisted reproduction is essential for optimizing reproductive success in UEI and ARI cases.