November 3, 2025

First Time, Long Time, by Amy Silverberg

I picked up Amy Silverberg’s debut novel after Maris Kreizman called it “this year’s Margot’s Got Money Troubles, a book that poses big questions with both confidence and a breeziness and that will keep you wanting to turn the pages.” And First Time, Long Time, did not let down, though I wasn’t entire sure about it as I was reading, sure of what all the pieces would add up to. Because indeed this a novel comprised of fragments, just as protagonist Allison’s entire life is. She works various jobs—hosting book clubs for rich ladies, and teaching junior college among them—while living in a studio apartment in Los Angeles where she’s trying to launch her writing career and make a fresh start after the death of brother, which looms large in her mind, all the while her divorced parents continue to torment her in their own ways. And one night when she’s out at a bar, she meets a man she at first pretends not to know, but knows him, she does. He’s Reid Steinman, a famous radio DJ whose voice haunted her childhood from when her father was a fan. Inspired by Howard Stern, Steinman is a similarly complicated character who contains multitudes, as Allison learns for herself once they get together and begin a relationship, the daddy issues only multiplying once Allison also gets somewhat involved with Steinman’s 20-something daughter.

“Wait, did you just give away the whole plot?” asked a friend in my group chat where I’d been recommending this book, and I replied that I sure hadn’t. Silverberg, who is also a comedian, turns out to the a master of the set-up, one I’d spent the novel wondering about even as I was breezily turning the pages as Kreizman predicted. Where could this novel of twisted, broken and mirrored family ties, and unsatiated appetites possibly be leading, I’d wondered, but oh, just you wait. The climax is unforgettable, impeccable, perfect, and it leads to the most wonderful final paragraph I’ve encountered in any novel ever.