As AI becomes an increasingly pervasive force in modern software development, it is reshaping how systems are created, reviewed, and evolved across the software lifecycle. At the same time, technical debt remains an inescapable reality, weighing on maintenance effort, change velocity, and system reliability. This keynote focuses on the intersection where these two forces meet and the questions it raises for both researchers and practitioners: What happens when AI and technical debt intersect? Will they be friends – or will they turn into foes? This keynote will explore these questions, highlighting empirical findings, existing challenges, and future directions at the exciting intersection of technical debt and AI4SE.