Where do Madeleine and Silas meet again?

They meet again at the hospital after she returns to the 21st century.

What event triggers Madeleine’s return to the 21st century?

A tenth-anniversary scandal linking Silas to her best friend triggers her return.

System Reboot: Goodbye, Commander

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System Reboot: Goodbye, Commander — Madeleine Vance saves Silas Thorne through the System, marries him, then returns to the 21st century after a tenth-anniversary scandal.

Madeleine Vance trades years of her life through the System to rescue her dying grandmother, and the same bargain pulls Silas Thorne away from a doomed fate. She falls for him, marries him, and remains at his side for a decade. On their tenth wedding anniversary, she discovers a scandal linking Silas to her best friend and activates the System to send herself back to the 21st century. At the hospital she finds Silas waiting there too, restored by that same System.

Quick answers

Where do Madeleine and Silas meet again?: They meet again at the hospital after she returns to the 21st century.
What event triggers Madeleine’s return to the 21st century?: A tenth-anniversary scandal linking Silas to her best friend triggers her return.