The choice of treatment in case of ovarian endometriomas is one of the most discussed topics in Reproductive Medicine. Management options include expectancy, medical treatment, surgery, in vitro fertilization (IVF), or a combination of the above. The main presenting symptom, i.e. pain or infertility, usually guide the choice of treatment. Medical treatment is usually preferred as the first line option when pain is the associated symptom, whereas surgery or IVF are preferred in case of associated infertility. In most cases, however, the symptoms may overlap, and often a patient with infertility complains also of chronic pelvic pain, and vice versa. In addition, in many cases the patient may be asymptomatic, usually presenting with the incidental diagnosis of an ovarian endometrioma. Therefore, a strict categorization in two separate pathways of either associated pain or associated infertility, as the one outlined in current guidelines, may not represent the real clinical scenario. In this context, a personalized approach, taking into account several additional variables that are not considered in guidelines, is mandatory. In the present review, a symptom-driven approach to the management of ovarian endometriomas, that goes beyond the pain/infertility categorization, is described, considering additional parameters that guide the choice of treatment, with a patient-centered, personalized approach.