In Julia Rajagopalan’s “Missing Things,” two old friends meet for coffee carrying years of shared history—and a conversation neither of them wants to have.

In Abriana Jetté’s “What We Chat About When We Chat About Chat,” a lonely newcomer to New York finds herself questioning where human connection ends and artificial companionship begins. Wry, unsettling, and unexpectedly tender, the story asks what it really means to need—and be needed by—someone.

“We'll be Friends Forever, won't we, Pooh?” asked Piglet. “Even longer,” Pooh answered. A. A. Milne My childhood and adolescence were...

1 It was a cool fall evening, the sky gray and the air still. I tied the goldenrod with a blue ribbon and held it in my hand as I walked,...