Abstract Personal humorous remarks may be avoided in certain conversations out of fear of introducing and reinforcing undesirable assumptions. Teases directed at others and self-targeted humor are perhaps the most vulnerable in this regard. Unless participants know each other well, a tease intended as kidding could be heard as an insult, and a self-directed remark could be read as a confession. When humor is not expected, speakers may have to rely more heavily on presentational cues, such as prior humorous context or exaggeration to mark humorous intent, or pretense. We examined variation in conversational humor in 59 transcripts of naturally occurring conversations of mixed- and same-sex groups of friends. We looked specifically at whether speakers were less likely to show high-cost forms of humor, such as self-targeting and teasing, in contexts where a listener's recognition of pretense would be relatively low—i.e., teasing of men by women and women by men in mixed-sex interactions. In mixed- compared to same-sex groups, European American men teased less and made self-directed wisecracks more, and European American women teased more but told fewer humorous stories about themselves. Exaggeration as a mode of flagging humor occurred in self-directed wisecracks of both men and women, and in teasing by women in mixed groups and by men in all-male groups. Risky humor in mixed groups was also more likely to occur as a continuation of an earlier humorous key. We explain our results in terms of gender role expectations involving aggression, power, and self-disclosure as they relate to the interpretation of humor in conversation.