For many, disclosing romantic feelings in a friendship poses a threat to that relationship. At the very least, the relationship becomes complicated. Disclosure can cause relationship renegotiation, but it can also cause the friendship to end. Using Communication Privacy Management theory (CPM) as a framework, this study investigated the decision-making process for disclosing romantic feelings to a cross-sex friend, as well as the strategies used to manage privacy boundaries. Thirty-two in-depth qualitative interviews were completed, where participants shared their experience of being in a cross-sex friendship where they had feelings for their friend. Interview transcripts were analyzed thematically using an open coding approach. The risk-benefit ratio, primarily oriented around relational consequences, was the most influential in participants' decision-making about disclosure and avoidance. The risks and benefits participants perceived were influenced by their certainty or uncertainty surrounding their friend's feeling for them. Participants experienced three types of relational uncertainty, self-uncertainty, partner uncertainty, and relationship uncertainty. All types of uncertainty affected the decision-making process regarding disclosure of their feelings. Contextual criteria, personality, and gender criteria were also influential for participants. Participants' strategies for disclosure included disclosing directly, indirectly, reciprocally, or avoiding disclosure or engaging in some combination of these strategies. Expanding on theory, this study suggests disclosure criteria provided by CPM are only part of the decision-making process and the uncertainty participants experience is influential in their choices about disclosure.