Previous task complexity studies have suggested that learners produce more negotiation of meaning opportunities during complex tasks than simple tasks (Robinson, 2011). The present study builds on the existing task complexity literature by examining the impact of task complexity and pragmatic situational demands on the number of learning opportunities for request-making expressions. Forty-nine Korean junior high school learners of English as a foreign language were randomly assigned to participate in either simple- or complex-collaborative pair writing tasks, which included different levels of pragmatic situational demands. The interactions were transcribed and analyzed for the frequency of pragmatic related episodes (PREs; Kim & Taguchi, 2015) as well as the number of turns within each PRE. The results showed that task complexity played an important role in facilitating PREs by targeting sociopragmatic factors and not pragmalinguistic forms, regardless of the level of pragmatic task demands. Results are discussed in light of promoting interaction-driven learning opportunities for pragmatics using collaborative tasks.