The math governing Einstein-Rosen bridges (the “wormholes” beloved of scifi writers who ignore physics) indicates that the E-R bridge expands faster than it can be traversed. So even if an object could survive the process of entering a black hole that object would never exit. Likewise Alice and Bob, entering a pair of entangled black holes (Alice enters Hole1, Bob enters Hole2) and assuming their survival, could meet in the theoretical middle but would remain there forever. As and when a black hole evaporates by means of Bekenstein-Hawking radiation whatever was inside the hole does not magically reappear; its entropic value is returned to the external universe, which is a very different thing indeed. It’s nice to popularize science but important to ensure the basic facts are properly understood and conveyed. Professor Leonard Susskind has a series of informative lectures covering all these topics and more on YouTube; the math is not overly complicated to follow, and the key concepts are conveyed clearly.