This paper provides a general method for establishing finite-time singularity formation for moving interface problems involving the incompressible Euler equations in the plane. This methodology is applied to two different problems.The first problem considered is the two-phase vortex sheet problem with surface tension, for which, under suitable assumptions of smallness of the initial height of the heaviest phase and velocity fields, is proved the finite-time singularity of the natural norm of the problem. This is in striking contrast with the case of finite-time splash and splat singularity formation for the one-phase Euler equations of [4] and [8], for which the natural norm (in the one-phase fluid) stays finite all the way until contact.The second problem considered involves the presence of a heavier rigid body moving in the inviscid fluid for which well-posedness was recently established in [16]. For a very general set of geometries (essentially the bottom of the symmetric domain being a graph) we first establish that the rigid body will hit the bottom of the fluid domain in finite time. This result allows for more general geometries than the ones first considered by [19] for this problem, as well as for small square integrable vorticity. Next, we establish the blow-up of a surface energy and a characterization of acceleration at contact: It opposes the motion, and is either strictly positive and finite if the contact zone is of non zero length, or infinite otherwise.