Many older men are not experienced in cooking, which may create challenges for those who might need to prepare their own meals in the future. By developing an understanding of older men's cooking experiences, designers may have the insights needed to design interventions to support this population's cooking experiences. This preliminary study worked with two different participant groups, older men (ages 65 years and older) with limited cooking experience, and designers from relevant design fields. Three qualitative and exploratory design research methods were used: interviews and journal-based cultural probe kits with the older men; and focus groups with designers using personas derived from the first two methods. From these methods' insights, an understanding into the perspectives of older men cooking was produced; including three primary themes relevant to design. Additionally, two recommendation categories were created through insights produced for designers aiming to facilitate older men's cooking experiences through design intervention.