We introduce a Monte Carlo scheme for sampling a bold-line diagrammatic series specifying an unknown function in terms of itself. The range of convergence of this bold(-line) diagrammatic Monte Carlo (BMC) technique is significantly broader than that of a simple iterative scheme for solving integral equations. With the BMC technique, a moderate "sign problem" turns out to be an advantage in terms of the convergence of the process. For an illustrative purpose, we solve the one-particle s-scattering problem. As an important application, we obtain the T matrix for a Fermi polaron (one spin-down particle interacting with the spin-up fermionic sea).