Given that male-female friendships lack institutional guidelines or scripts to guide everyday interactions, sustaining these relationships can be complicated. Although researchers have recently begun to study relational maintenance patterns in cross-sex friendships, no study has yet to investigate sex's and dating status's direct influences on friendship maintenance. This investigation seeks to add to the field's academic understanding of these personal relationships. Specifically, the researcher sought to uncover the associations between 10 friendship maintenance behaviors, past sexual contact, valence of past sexual contact, and cross-sex friends' dating statuses. Quantitative data were collected from 277 participants at a large Southeastern university using a survey methodology. Overall, results indicate that patterns of relational maintenance do differ as a function of friendship level, past sexual involvement, valence of past sexual involvement, and cross-sex friends' dating statuses. Past sexual involvement associates with higher levels of relationship talk, avoidance of negativity, and flirting. In addition, valence of past sexual activity varies across friendship level and associates with higher levels of positivity and flirting. Lastly, dating status significantly affects 3 of the 10 maintenance behaviors: routine contact and activity, flirting, and humor. Linear, quadratic, and cubic relationships were found for these variables, respectively. Implications of results, limitations, and recommendations for future research are discussed.