We construct several models to describe the scenario where two eternal black holes are entangled by exchanging radiations. The increasing entanglement between two black holes is reflected in the emergence of a wormhole phase, which could be considered as an incarnation of ER = EP R conjecture. In the context of double holography, we compute the holographic entanglement entropy and the mutual information among of various partitions in the bulk and obtain the phase structure of the entanglement for the system. We find that two black holes, which could be either equal in size or not, can be entangled as long as they are not far apart; in general, the formation of a wormhole needs to overcome the distance between two black holes, and unitarity is preserved by either the formation of a wormhole or the emergence of islands. When the sizes of two black holes are not equal, we observe a loss of entanglement between the smaller black hole and the radiation at late times. We further compute the same entropy measures on the field theory side by considering a coupled SYK model at finite N , where two SYK models are applied as the dual description of two black holes and a Majorana chain connecting them resembles the radiation region. We explicitly compute the entanglement among two SYK systems and the chain, and obtain the similar phase structure as the bulk results. In general, a time delay of entanglement between two SYK sites is found in cases with longer Majorana chains. In particular, when two SYK sites are different in size, similar entanglement loss between the SYK cluster with fewer fermions and the radiation region are observed. To have a more intuitive understanding on the evolution of the entanglement, we further investigate a chain model composed of EPR clusters where exchanging particles are only allowed between neighbouring clusters. In this model, the outermost clusters serve as two black holes, and all inner clusters serve as the radiation. Despite the drastic simplification, the main features observed in previous models persist in this model, including the feature of entanglement between outermost clusters, the time delay of entanglement between two black holes due to distance, and the entanglement loss.