Engaging with those we disagree with is necessary in almost all aspects of our lives. Philosophers and scientists have long proposed how discussions involving disagreement should take place. In the current research, we focus on two possible styles of engagement when people disagree: dialogue and debate. We conceptualize a dialogue-like discussion as one where the goal is to understand one another’s perspectives completely and accurately while in a debate-like discussion the goal is to convince the other person that one’s view is correct. Given these possible ways of engagement, we explored the situational features that lead people to spontaneously engage in one mode or the other. In three online scenario studies we found evidence that in a conversation where two people disagree, caring about the conversation partner’s impression of them, when the conversation partner’s goal was to learn from them, and belonging to the same political party pushed people to have a more dialogue-like conversation. On the other hand, discussing a moral issue, feeling certain about one’s position, and having a high level of disagreement led to a more debate-like conversation. Lastly, people’s desire to engage in a dialogue may be mediated by whether they feel they have shared goals and values with the person they are speaking with.