The optimal matching of point clouds in $\mathbb{R}^d$ is a combinatorial problem; applications in statistics motivate to consider random point clouds, like the Poisson point process. There is a crucial dependance on dimension $d$, with $d=2$ being the critical dimension. This is revealed by adopting an analytical perspective, connecting e.\,g.~to Optimal Transportation. These short notes provide an introduction to the subject. The material presented here is based on a series of lectures held at the International Max Planck Research School during the summer semester 2022. Recordings of the lectures are available at https://www.mis.mpg.de/events/event/imprs-ringvorlesung-summer-semester-2022.