The current study provided an exploratory mixed methods investigation of the messages undergraduate men received about sex and relationships from their male and female friends. Participants included 310 undergraduate men who provided written responses regarding the specific messages they had received from male and female friends. Descriptive codes included: just do it, meaningful intimacy, gentlemen, postpone sex, women’s sexual desire, and objectification of women. Reports of sexual communications were typically consistent with the Heterosexual Script and congruent with the friend’s gender. Accordingly, reports of male friends’ communications often portrayed the accumulation of sexual experiences and partners as necessary and desirable, whereas serious, romantic relationships were often portrayed as hindrances. Reports of female friends’ messages, in contrast, primarily focused on the importance of romantic relationships and the idealization of sex within such relationships. Reports of messages that were incongruent with the Heterosexual Script were rare, and were more often found in reports of female friends’ communications. For example, female friends were the only source of messages regarding women’s sexual needs, desires, and pleasures. By documenting patterns of common and uncommon messages and their sources, the present study contributed insights into how male and female friends similarly and differentially reinforce different dimensions of hegemonic masculinity.