Pickleworm, Diaphania nitidalis Cramer (Lepidoptera: Crambidae), is a major pest of cucurbits. The current management approach for this pest is weekly insecticide applications. A push–pull cropping approach may be an alternative management practice and could reduce reliance on pesticides. One potential push–pull scenario is the use of squash (Cucurbita pepo L.) as a trap crop and watermelon (Citrullus lanatus [Thunb.] Matsum. & Nakai) as a deterrent intercrop to manage pickleworm on cantaloupe (Cucumis melo L.). This study investigated if the underlying mechanism required for the success of this management approach (a female oviposition preference or nonpreference among squash, cantaloupe, and watermelon) is present. A series of oviposition preference experiments was conducted to see how individual females responded when presented with different host plants for oviposition. Under laboratory conditions, when females had the choice of a leaf from squash, cantaloupe, and watermelon, they laid a higher proportion of their eggs on the cantaloupe leaf. However, under greenhouse conditions, when females were presented with whole plants of the three different species, they laid a higher percent of their eggs on the squash plant. Females laid a similar number of eggs on watermelon as compared with cantaloupe under greenhouse conditions, and appeared to not be averse to laying their eggs on watermelon. However, when presented with a noncucurbit, such as bean, females laid a low number of total eggs. Overall, it appears that squash may be more preferred as an oviposition substrate than cantaloupe or watermelon and may be a useful trap crop or pull. Further study to determine a suitable deterrent intercrop or push and evaluation of the proposed system under field conditions are needed.