Hysteroscopy is known to be the gold standard for evaluation of intrauterine pathologies, pre-menopausal and post-menopausal abnormal uterine bleeding and, in addition to this, it is a crucial examination in the infertility work-up. In-office operative hysteroscopy incorporates the outstanding possibility of seeing and treating an intracavitary pathology in the same examination, eliminating all the risk related to anesthesia and reducing procedure-related costs. By now, performing operative procedures in the office setting is recognized as feasible and safe. Over the last 20 years, many efforts have been made to implement the in-office operative approach worldwide. However, for some women, in-office hysteroscopy is still considered a painful experience, with reported discomfort at different steps of the hysteroscopic procedures. Moreover, uneventful and tedious sensations might be increased by a high level of anxiety for such examination. For this reason, despite the feasibility of the in-office approach, many clinicians are still afraid of provoking pain during the procedure and rather not to perform surgical procedures in the office, postponing the removal of the pathology in the operating room. To date, there is no consensus concerning pain management for in-office hysteroscopy and different approaches, pharmacological and non-pharmacological aids, as well as several procedural tips and tricks are utilized. Our purpose is to provide a feasible practical decalogue for the operator, to supply adequate management of pain during in-office hysteroscopic procedures, performing challenging operations, shrinking discomfort, aiming to upgrade both women’s and operator’s satisfaction.