First, a question about the title. Why did you choose it?

A lot of people go through life professing to have no regrets, almost as if regret is a sign of weakness or loser-dom. I chose the title because it’s so counterintuitive. No one wants to have any regrets, or even admit to them. Jeremy Best, one of the two lead characters of this novel, admits he regrets everything. Mind you, he is only able to own his failures by convincing himself he can live with the results. Wrapped in the trappings of a successful legal career, he surveys his abandoned literary calling and indifferent love life with fatalistic humor. This outlook is challenged by the arrival of Spaulding Simonson; she makes him truly consider the ramifications of his actions and then shift gears. And I like that “I Regret Everything” is a play on the title of the Edith Piaf song.

Does Jeremy truly regret everything?

He regrets all the major decisions in his life, starting with walking away from a great love when he was young, then abandoning a promising career as a poet to become a trusts and estates lawyer, something he finds considerably less satisfying. If we accept Freud’s dictum that love and work are the cornerstones of our humanness then, yes, Jeremy regrets everything because he’s screwed up his humanness.

Is his affair with Spaulding a regret too?

Although he enters into the affair with Spaulding with understandable reluctance, he does not regret it because it’s his involvement with her that changes his outlook and frees him from the prison he’s constructed for himself.

You’ve written before about non-traditional love stories, notably in your work on the HBO series, Big Love. How was writing the love story between Jeremy and Spaulding different from your previous work?

It’s shorter, for starters. I don’t mean that to be glib, either. I Regret Everything is a compact story about two characters who fall in love. There isn’t a lot of extraneous stuff going on.

It’s a complete departure for me in that it is a love story, something I’ve never attempted in fiction. But it does have antecedents in the work I did on Big Love, which, since it dealt with polygamy, was non-traditional in the extreme.

I’ve never written a book where such a young character has carried so much of the narrative. And although I’ve written novels where female characters have played large roles, I’ve never written one where a woman was quite this integral. It was different, also, in that the book is written in alternating first person accounts, so the reader follows the development of their attraction from two totally different perspectives. And since people – and fictional characters – are finally unknowable to themselves, the book has not one, but two unreliable narrators.

The age difference between Jeremy and Spaulding never becomes a factor in this love story and doesn’t seem to matter at all (except to Spaulding’s father, Jeremy’s boss). Are we too hung up on age? Are you saying age doesn’t matter?

My father was ten years older than my mother. Their marriage lasted thirty-six years so I’m probably biased. I Regret Everything is a story about how an aspiring poet pursues an older one, who does not welcome the pursuit, primarily because he works for her father, but also, yes, because of her age. Would the story work if Jeremy and Spaulding were the same age? It wouldn’t be as provocative, certainly. Writing a love story is a challenge in this era because love stories depend on the obstacles that keep the characters apart. Differences of race, religion, or nationality largely elicit shrugs today but differences of age can still ring the outrage bell. To be clear, I didn’t design their age difference to be provocative because I don’t consider it to be a big deal. We’re on this planet for the blink of an eye. I’ve already survived a near death experience. If a nineteen year old woman falls for someone who’s thirty-three and he, after much consideration, reciprocates, who am I to suggest they not pursue mutual happiness? Is it moral if they don’t get together? I don’t think so. What is more moral than love? These are two smart, talented people who, before they meet, have lived largely in their own heads. He’s not consumed with lust for Spaulding as soon as he sees her. Rather, he finds himself drawn in as her talent, psychological complexity and joie de vivre reveal themselves and awaken dormant qualities in him. It is only after a violent incident rocks the two of them that he realizes what she has come to mean to him. When he can no longer pretend he’s not in love with her, the bonds of propriety unravel.

Jeremy is a trusts and estates attorney and also a published poet. These two careers seem like they are at opposite ends, but you say they overlap more than one might expect.

On a basic level, a trusts and estates lawyer and a poet are both writers. And both jobs involve the act of distillation. A T&E lawyer distills the wishes of a client at the end of a life into a binding legal document while a poet wrings some kind of crystalline thought from the chaos of her brain and renders it as verse on a page, comprehensible and – she hopes – aesthetically pleasing. Also, both jobs have their eyes on eternity.

How is this novel the story (or not) of your life, and the choices you did or didn’t make?

From the time I was old enough to think about a career my father suggested I become a lawyer. He grew up poor in the Bronx and saw the legal profession as an exalted thing, something that would provide a life of security and prestige. I went so far as to take the law boards when I was a college senior where I had a Saint Paul on the road to Damascus moment and knew I could never be a member of the bar. Had I become a lawyer, it would have been a major regret. Not that there’s anything wrong with being a lawyer. My wife and my oldest friend are both attorneys. But I wanted to delve into a lot of different worlds and lead a more varied, less settled life. The best way for me to do that was to become a writer.

Jeremy’s mother spends time in Bellevue and kills herself in front of her family, including Jeremy. When Jeremy first meets Spaulding, the boss’s daughter, she’s just completed time in a mental hospital. Why does mental instability play a large role in this novel?

Great poets, sadly, have a vivid history of mental instability and suicide. It’s like jazz musicians and heroin, an occupational hazard. Sylvia Plath, John Berryman, Hart Crane; it’s a sad list and it goes on. Jeremy, like Allen Ginsberg, had a mother who was mentally ill. A lot of poets perceive reality in a heightened way. It can be unbearable. To write a story about two poets who were perfectly well adjusted would have been fake.

A random act of violence occurs in the heart of the novel — Can you talk about this scene in the suburbs?

In the story this violent act works almost like the breaking of a fever. When Spaulding moves to the suburbs she’s freaked out by the physical nature of the environment. She anthropomorphizes the trees and ascribes insidious intent to something as simple as the movement of their branches in the wind. This is a reaction that reflects her general anxiety. But the violent act that occurs is real and the way she handles it, rather than wigging her out, gives her new confidence in dealing with the internal demons that plague her. It also allows Jeremy to play a traditionally heroic role, something he would never ordinarily do since he views himself as anything but a hero. It reshuffles both the characters and the story.

Like Jeremy, you were once diagnosed with life-threatening cancer. What did that experience bring to your writing this novel and to your life?

When I was in my thirties, like Jeremy, I was diagnosed with stage four cancer. When I hear people talk about “the gift of cancer” I think, sure, if bowel-shaking fear is a gift. Mostly, I remember the sheer terror. But along with the terror was the deep sadness that my life might end way before I was ready. I also began to perceive reality differently. My tolerance for bullshit plummeted. Little things didn’t upset me as much. And I focused on what I wanted to get done. What cancer does to a young person is adjust their naturally (and normal) naïve approach to mortality. All of this came into play in the creation of Jeremy’s character. His decision to get involved with Spaulding comes right out of his having cancer. And because of that decision his life becomes immeasurably richer. So along with the bowel-shaking fear he finds love. Maybe it is a gift. Actually, no. It was horrible.

Do you have any regrets?

There are people who I didn’t treat as well as I should have. There are risks I didn’t take. There are relationships I stayed in longer than was healthy. Here’s my biggest regret: I met my wife at a party in New York. She was with her fiancé and I was with my girlfriend. I fell for her instantly, and then didn’t see her for another for five years. I regret that we didn’t run off together that day.

I Regret Everything, while laugh out loud funny in parts, is more serious than your previous books. What do you hope readers take from this story?

Regret is way underrated. To regret something implies you’ve thought about it, reflected and evolved. Embrace your regrets. Learn from them. Don’t hate yourself. The fire will either melt us, or forge us. It’s a choice.