Tens of thousands of senior medical students interview for medical residency positions each year. As the applicant pool shifts to include more women, married individuals, and young parents, the criteria by which interviewees evaluate programs are also changing. Concerns including parental leave policies, lactation facilities, access to childcare, partner recruitment resources, and inclusivity in the work environment are important in selecting an ideal program. However, the National Resident Matching Program Match Communication Code of Conduct prohibits interviewers from addressing gender, marital status, and intent to bear children, so the burden of introducing such topics falls on the interviewees. These topics can be difficult to discuss with potential employers, especially when weighed against the pressure to obtain a competitive position through the Match. In this Invited Commentary, the authors draw on personal experience to examine the questions that residency programs need to answer, encouraging both applicants and programs to improve communication during the residency interview process.