Over the last few decades, reproductive medicine has observed an improvement in the management and outcome of pregnancy in connective tissue diseases, such as systemic lupus erythematosus (SLE) and antiphospholipid syndrome (APS). However, pregnancy and related issues remain a challenge in these patients. In routine clinical practice, health professionals dealing with SLE and APS need to consider the numerous aspects of the reproductive life of their patients, such as pregnancy, family planning, fertility, contraception, cancer surveillance, and menopause. The new European League Against Rheumatism recommendations for women's health and family planning reflect the need for a novel approach to communication in the patient-physician relationship. Preconception counseling is essential to ensure optimal pregnancy outcomes through a careful risk stratification involving disease activity, organ involvement, autoantibody profile, use of drugs, and previous pregnancy outcomes, as well as to ensure better preventive and therapeutic strategies to limit complications. In patients with stable/inactive disease and low risk of thrombosis, adequate hormonal contraception and menopausal replacement therapy should be recommended. Assisted reproductive techniques can be safely used in these patients, but anticoagulation or low-dose aspirin (or both) should be added in those with positive antiphospholipid antibody titers. All menstruating women should be counseled on the possibility to preserve fertility with gonadotropin-releasing hormone analogues if receiving alkylating agents. Strict clinical, serological, laboratory, and multidisciplinary monitoring during pregnancy is mandatory to early recognize and effectively treat disease flares or obstetric complications. Doppler ultrasonography and fetal biometry should be regularly performed, especially in the second and third trimesters. Physicians should recommend screening for cervical dysplasia related to human papillomavirus (HPV) infection, especially during immunosuppressive therapy, and HPV immunization can be used in women with stable/inactive disease.