The classical flexibility difference method detects damage by observing the difference of conventional deflection flexibility matrices between pre- and post-damaged states of a structure. This method is not able to identify multiple damage scenarios, and its criteria to identify damage depend upon the boundary conditions of structures. The key point behind the inability and dependence is revealed in this study. A more feasible flexibility for damage detection, the Angle-between-String-and-Horizon (ASH) flexibility, is proposed. The physical meaning of the new flexibility is given, and synthesis of the new flexibility matrix by modal frequencies and translational mode shapes is formulated. The damage indicators are extracted from the difference of ASH flexibility matrices between the pre- and post-damaged structures. One feature of the ASH flexibility is that the components in the ASH flexibility matrix are associated with elements instead of Nodes or DOFs. Therefore, the damage indicators based on the ASH flexibility are mapped to structural elements directly, and thus they can pinpoint the damaged elements, which is appealing to damage detection for complex structures. In addition, the change in the ASH flexibility caused by damage is not affected by boundary conditions, which simplifies the criteria to identify damage. Moreover, the proposed method can determine relatively the damage severity. Because the proposed damage indicator of an element mainly reflects the deflection change within the element itself, which significantly reduces the influence of the damage in one element on the damage indicators of other damaged elements, the proposed method can identify multiple damage locations. The viability of the proposed approach has been demonstrated by numerical examples and experimental tests on a cantilever beam and a simply supported beam.