Developing future high performance adhesives is predicated upon achieving properties including strength and ductility. However, designing tough materials that are simultaneously strong and soft is usually contradictory in nature. Biological materials including shells and wood achieve impressive toughness by using weak bonds to connect larger structures at several length scales. Here, we show that this toughness design approach can be applied to synthetic adhesives. A biomimetic adhesive polymer, poly(catechol-acrylic acid), was examined in conjunction with several compounds containing two organic functional groups. In a typical example, the diol ethylene glycol decreased the overall system modulus. Performance was seen to increase significantly. Spectroscopic and physical methods indicated that these bifunctional additives created an interpolymeric network of weak hydrogen bonds. Material toughness was enhanced when breakable bonds were available to dissipate mechanical stresses while leaving the surrounding matrix intact. These discoveries illustrate how a biological materials strategy of interplay between strength and ductility can be achieved with sacrificial bonds in an adhesive. Such an approach may be a general principle applicable to designing higher performance electronics, transportation, and aerospace systems.