Refracturing is an important technology for tapping remaining oil and gas areas and enhancing recovery in old oilfields. However, a complete and detailed refracturing timing optimization scheme has not yet been proposed. In this paper, based on the finite volume method and the embedded discrete fracture model, a new coupled fluid flow/geomechanics pore-elastic-fractured reservoir model is developed. The COMSOL 3.5 commercial software was used to verify the accuracy of our model, and by studying the influence of matrix permeability, initial stress difference, cluster spacing, and fracture half-length on the orientation of maximum horizontal stress, a timing optimization method for refracturing is proposed. The results of this paper show that the principle of optimizing the refracturing timing is to avoid the time window where the percentage of Type I (Type I indicates that stress inversion has occurred, 0∘≤α≤20∘; Type II indicates that the turning degree is strong, 20∘<α≤70∘; and Type III indicates less stress reorientation, 70∘<α≤90∘) stress reorientation area is relatively large, so that the fractures can extend perpendicular to the horizontal wellbore. At the same time, the simulation results show that with the increase in production time, the percentage of Type I and Type II increases first and then decreases, while the percentage of Type III decreases first and then increases. When the reservoir permeability, stress difference, and cluster spacing are larger, the two types of refracturing measures can be implemented earlier. But, with the increase in fracture half-length, the timing of refracturing Method I is earlier, and the timing of refracturing Method II is later. The research results of this paper are of great significance to the perfection of the refracturing theory and the optimization of refracturing design.