Below, a "disk" means a compact subspace $D \subset \mathbb R^2$ whose boundary is a smooth simple closed curve.
Task: Find a procedure which takes as input a pairs of disks $ D_0 \subseteq D_1 $ in the plane, and produces as output a smooth 1-parameter family of disks that interpolates between them: $$ \{D_t\}_{t \in [0,1]}. $$ The family should be monotonic in the sense that $ t_1 \le t_2 \Rightarrow D_{t_1} \subseteq D_{t_2}. $
The procedure should furthermore be (continuous and) smooth, meaning that if we have a family of pairs $D_0(x) \subseteq D_1(x)$ depending smoothly on some parameter $x\in\mathbb R^n$, then the output of the procedure $\{D_t(x)\}_{t \in [0,1]}$ should depend smoothly on $(t,x)\in [0,1]\times\mathbb R^n$.
Remark: If $D_0$ is contained in the interior of $D_1$, then the level curves of the solution of the Dirichlet problem on $D_1 {\setminus} \mathring D_0$ with boundary values $0$ on $\partial D_0$ and $1$ on $\partial D_1$ provide a family of simple closed curves interpolating between $\partial D_0$ and $\partial D_1$ (hence a family of disks interpolating between $D_0$ and $D_1$). This procedure has all the desired good properties, but it doesn't obviously work when $\partial D_0 \cap \partial D_1 \neq \emptyset$.