A Langmuir film is a molecularly thin film on the surface of a fluid; we study the evolution of a Langmuir film with two coexisting fluid phases driven by an interphase line tension and damped by the viscous drag of the underlying subfluid. Experimentally, we study a 4′-8-alkyl[1,1′-biphenyl]-4-carbonitrile (8CB) Langmuir film via digitally imaged Brewster angle microscopy in a four-roll mill setup which applies a transient strain and images the response. When a compact domain is stretched by the imposed strain, it first assumes a bola shape with two tear-drop shaped reservoirs connected by a thin tether which then slowly relaxes to a circular domain which minimizes the interfacial energy of the system. We process the digital images of the experiment to extract the domain shapes. We then use one of these shapes as an initial condition for the numerical solution of a boundary-integral model of the underlying hydrodynamics and compare the subsequent images of the experiment to the numerical simulation. The numerical evolutions first verify that our hydrodynamical model can reproduce the observed dynamics. They also allow us to deduce the magnitude of the line tension in the system, often to within 1%. We find line tensions in the range of 200–600 pN; we hypothesize that this variation is due to differences in the layer depths of the 8CB fluid phases.