Obesity is the cause of up to one-third of all cancers affecting women today, most notably endometrial, colon and breast cancer. Women’s health providers are poised to advise women on obesity’s link to cancer development, but often lack resources or training to provide appropriate counseling. Here, we review obesity’s role in increasing the risk of several common reproductive system conditions faced by women, including polycystic ovarian syndrome, infertility, gynecologic surgical complications, and pregnancy complications. These events can be used as teachable moments to help frame the discussion of weight management and promote cancer prevention. We also review national guidelines and existing tangible weight-loss strategies that can be employed within the outpatient women’s health setting to help women achieve weight loss goals and affect cancer prevention.