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The Pursuit of Happiness

A Novel

About The Book

This international bestseller tells the incredible and heartbreaking love story of Sara and Jack as they learn to understand their differences in postwar New York.

“Kennedy tells his epic tale with a keen eye and brisk pace.... a winningly sincere love story.” —Publishers Weekly

Manhattan, Thanksgiving eve, 1945.

The war is over, and Eric Smythe’s party was in full swing. All his clever Greenwich Village friends were there. So too was his sister Sara, an independent, outspoken young woman, starting to make her way in the big city.And then in walked Jack Malone, a U.S. Army journalist just back from a defeated Germany, a man whose world view was vastly different than that of Eric and his friends.

This chance meeting between Sara and Jack and the choices they both made in the wake of it would eventually have profound consequences, both for themselves and for those closest to them for decades afterwards.

Set amidst the dynamic optimism of postwar New York and the subsequent nightmare of the McCarthy era, The Pursuit of Happiness is a great, tragic love story; a tale of divided loyalties, decisive moral choices and the random workings of destiny.



I FIRST SAW her standing near my mother’s coffin. She was in her seventies – a tall, angular woman, with fine grey hair gathered in a compact bun at the back of her neck. She looked the way I hope to look if I ever make it to her birthday. She stood very erect, her spine refusing to hunch over with age. Her bone structure was flawless. Her skin had stayed smooth. Whatever wrinkles she had didn’t cleave her face. Rather, they lent it character, gravitas. She was still handsome – in a subdued, patrician way. You could tell that, once upon a recent time, men probably found her beautiful.

But it was her eyes that really caught my attention. Blue-grey. Sharply focused, taking everything in. Critical, watchful eyes, with just the slightest hint of melancholy. But who isn’t melancholic at a funeral? Who doesn’t stare at a coffin and picture themselves laid out inside of it? They say funerals are for the living. Too damn true. Because we don’t just weep for the departed. We also weep for ourselves. For the brutal brevity of life. For its ever-accumulating insignificance. For the way we stumble through it, like foreigners without a map, making mistakes at every curve of the road.

When I looked at the woman directly, she averted her gaze in embarrassment – as if I had caught her in the act of studying me. Granted, the bereaved child at a funeral is always the subject of everybody’s attention. As the person closest to the departed, they want you to set the emotional tone for the occasion. If you’re hysterical, they won’t be frightened of letting rip. If you’re sobbing, they’ll just sob too. If you’re emotionally buttoned up, they’ll also remain controlled, disciplined, correct.

I was being very controlled, very correct – and so too were the twenty or so mourners who had accompanied my mother on ‘her final journey’ – to borrow the words of the funeral director who dropped that phrase into the conversation when he was telling me the price of transporting her from his ‘chapel of rest’ on 75th and Amsterdam to this, ‘her eternal resting place’ … right under the LaGuardia Airport flight path in Flushing Meadow, Queens.

After the woman turned away, I heard the reverse throttle of jet engines and glanced up into the cold blue winter sky. No doubt several members of the assembled graveside congregation thought that I was contemplating the heavens – and wondering about my mother’s place in its celestial vastness. But actually all I was doing was checking out the livery of the descending jet. US Air. One of those old 727s they still use for short hauls. Probably the Boston shuttle. Or maybe the Washington run …

It is amazing the trivial junk that floats through your head at the most momentous moments of your life.

‘Mommy, Mommy.’

My seven-year-old son, Ethan, was tugging at my coat. His voice cut across that of the Episcopalian minister, who was standing at the back of the coffin, solemnly intoning a passage from Revelations:

God shall wipe away all tears from their eyes;

And there shall be no more death, neither sorrow

Nor crying, neither shall there be any more pain;

For the former things are passed away.

I swallowed hard. No sorrow. No crying. No pain. That was not the story of my mother’s life.

‘Mommy, Mommy …’

Ethan was still tugging on my sleeve, demanding attention. I put a finger to my lips and simultaneously stroked his mop of dirty blond hair.

‘Not now, darling,’ I whispered.

‘I need to wee.’

I fought a smile.

‘Daddy will take you,’ I said, looking up and catching the eye of my ex-husband, Matt. He was standing on the opposite side of the coffin, keeping to the back of the small crowd. I had been just a tad surprised when he showed up at the funeral chapel this morning. Since he left Ethan and me five years ago, our dealings with each other had been, at best, businesslike – whatever words spoken between us having been limited to our son, and the usual dreary financial matters that force even acrimoniously divorced couples to answer each other’s phone calls. Even when he’s attempted to be conciliatory, I’ve cut him off at the pass. For some strange reason, I’ve never really forgiven him for walking right out of our front door and into the arms of Her – Ms Talking Head News-Channel-4-New-York media babe. And Ethan was just twenty-five months old at the time.

Still, one must take these little setbacks on the chin, right? Especially as Matt so conformed to male cliché. But there is one thing I can say in my ex-husband’s favor: he has turned out to be an attentive, loving father. And Ethan adores him – something that everyone at the graveside noticed, as he dashed in front of his grandmother’s coffin and straight into his father’s arms. Matt lifted him off the ground and I saw Ethan whisper his urination request. With a quick nod to me, Matt carried him off, draped across one shoulder, in search of the nearest toilet.

The minister now switched to that old funeral favorite, the 23rd Psalm.

Thou prepareth a table before me in the presence
of mine enemies; thou anointest my head with oil;
my cup runneth over.

I heard my brother Charlie choke back a sob. He was standing in the back of this sparse congregation of mourners. Without question, he had won the award for the Best Surprise Funeral Appearance – as he arrived at the chapel this morning off the red-eye from LA, looking ashen, spent, and deeply uncomfortable. It took me a moment to recognize him – because I hadn’t seen him in over seven years, and because time had worked its nasty magic, rendering him middle-aged. Okay, I’m middle-aged too –just!– but Charlie (at fifty-five, nearly nine years my senior) really looked… well, I guess mature would be the right word, though world-weary might be a little more accurate. He’d lost most of his hair, and all of his physique. His face had become fleshy and loose. His waist bulged heavily at both sides – a spare tire that made his ill-fitting black suit appear even more of a sartorial misjudgment. His white shirt was open at the collar. His black tie was dappled with food stains. His entire countenance spoke of bad diet and a certain disappointment with life. I was certainly on cordial terms with the last of these concepts … but I was still stunned at just how badly he had aged, and that he had actually crossed the continent to say goodbye to a woman with whom he had only maintained nominal contact for the past thirty years.

‘Kate,’ he said, approaching me in the lobby of the funeral chapel.

He saw my face register shock.


There was an awkward moment when he reached to hug me, then thought better of it and simply took my two hands in his. For a moment we didn’t know what to say to each other. Finally I managed a sentence.

‘This is a surprise …’

‘I know, I know,’ he said, cutting me off.

‘You got my messages?’

He nodded. ‘Katie … I’m so sorry.’

I suddenly let go of his hands.

‘Don’t offer me condolences,’ I said, my voice curiously calm. ‘She was your mother too. Remember?’

He blanched. Finally he managed to mumble, ‘That’s not fair.’

My voice remained very calm, very controlled.

‘Every day for the last month – when she knew she was going – she kept asking me if you had called. Towards the end, I actually lied, and said you were phoning me daily to see how she was doing. So don’t talk to me about fair.’

My brother stared down at the funeral home linoleum. Two of my mother’s friends then approached me. As they made the requisite sympathetic noises, it gave Charlie the opportunity to back away. When the service began, he sat in the last row of the funeral chapel. I craned my neck to check out the assembled congregation – and briefly caught his eye. He turned away in acute discomfort. After the service, I looked around for him, as I wanted to offer him the chance to ride with me in the so-called ‘family car’ to the cemetery. But he was nowhere to be found. So I traveled out to Queens with Ethan and my Aunt Meg. She was my father’s sister – a seventy-four-year-old professional spinster who has been devoted to the destruction of her liver for the past forty years. I was pleased to see that she had remained sober for the occasion of her sister-in-law’s send-off. Because on those rare occasions when she was practising temperance, Meg was the best ally you could have. Especially as she had a tongue on her like a pissed-off wasp. Shortly after the limo pulled away from the funeral home, the subject turned to Charlie.

‘So,’ Meg said, ‘the prodigal schmuck returns.’

‘And then promptly disappears,’ I added.

‘He’ll be at the cemetery,’ she said.

‘How do you know that?’

‘He told me. While you were pressing the flesh with everyone after the service, I caught him on the way out the door. “Hang on for a sec,” I told him, “and we’ll give you a ride out to Queens.” But he went all mealy-mouthed, saying how he’d rather take the subway. I tell you, Charlie’s still the same old sad asshole.’

‘Meg,’ I said, nodding toward Ethan. He was sitting next to me in the limo, deeply engrossed in a Power Rangers book.

‘He’s not listening to the crap I’m talking, are you, Ethan?’

He looked up from his book. ‘I know what asshole means,’ he said.

‘Attaboy,’ Meg said, ruffling his hair.

‘Read your book, darling,’ I said.

‘He’s one smart kid,’ Meg said. ‘You’ve done a great job with him, Kate.’

‘You mean, because he knows bad language?’

‘I love a girl who thinks so highly of herself.’

‘That’s me: Ms Self-Esteem.’

‘At least you’ve always done the right thing. Especially when it comes to family.’

‘Yeah – and look where it’s gotten me.’

‘Your mother adored you.’

‘On alternate Sundays.’

‘I know she was difficult…’

‘Try genteelly impossible.’

‘Trust me, sweetie – you and this guy here were everything to her. And I mean everything.

I bit my lip, and held back a sob. Meg took my hand.

‘Take it from me: parents and children both end up feeling that they’re the ones who landed the thankless job. Nobody comes out happy. But at least you won’t suffer the guilt that your idiot brother is now feeling.’

‘Do you know I left him three messages last week, telling him she only had days left, and he had to come back and see her.’

‘He never called you back?’

‘No – but his spokesperson did.’


‘The one and only.’

‘Princess’ was our nickname for Holly – the deeply resistible, deeply suburban woman who married Charlie in 1975, and gradually convinced him (for a long list of spurious, self-serving reasons) to detach himself from his family. Not that Charlie needed much encouragement. From the moment I had been aware of such things, I always knew that, for a mother and son, Mom and Charlie had a curiously cool relationship – and that the root cause of their antipathy was my dad.

‘Twenty bucks says Charlie-boy breaks down at the graveside,’ Meg said.

‘No way,’ I said.

‘I mightn’t have seen him in… when the hell did he last pay us a visit?’

‘Seven years ago.’

‘Right, it may have been seven years ago, but I know that kid of old. Believe me, he’s always felt sorry for himself. The moment I laid eyes on him today I thought: poor old Charlie is still playing the self-pity card. Not only that, he’s also got hot-and-cold running guilt. Can’t bring himself to talk to his dying mom, but then tries to make up for it by putting in a last-minute appearance at her planting. What a sad act.’

‘He still won’t cry. He’s too wound tight for that.’

Meg waved the bill in front of me.

‘Then let’s see the color of your cash.’

I fiddled around in my jacket pocket until I found two tens. I brandished them in front of Meg’s eyes. ‘I’m going to enjoy taking your twenty off you,’ I said.

‘Not as much as I’m going to enjoy watching that pitiful shithead weep.’

I cast a glance at Ethan (still buried in his Power Rangers book), then threw my eyes heavenward.

‘Sorry,’ Meg said, ‘it just kind of slipped out.’

Without looking up from his book, Ethan said, ‘I know what shithead means.’

Meg won the bet. After a final prayer over the coffin, the minister touched my shoulder and offered his condolences. Then, one by one, the other mourners approached me. As I went through this receiving-line ritual of handshakes and embraces, I caught sight of that woman, staring down at the headstone adjoining my mother’s plot, studying the inscription with care. I knew it off by heart:

John Joseph Malone
August 22, 1922-April 14, 1956

John Joseph Malone. Also known as Jack Malone. Also known as my dad. Who suddenly left this world just eighteen months into my life – yet whose presence has always shadowed me. That’s the thing about parents: they may physically vanish from your life – you may not have even known them – but you’re never free of them. That’s their ultimate legacy to you – the fact that, like it or not, they’re always there. And no matter how hard you try to shake them, they never let go.

As my upstairs neighbor, Christine, embraced me, I glanced over her shoulder. Charlie was now walking towards our father’s grave. The woman was still standing there. But once she saw him coming (and evidently knowing who he was), she immediately backed away, giving him clear access to Dad’s plain granite monument. Charlie’s head was lowered, his gait shaky. When he reached the gravestone, he leaned against it for support – and suddenly began to sob. At first he tried to stifle his distress, but within a moment he lost that battle and was sobbing uncontrollably. I gently removed myself from Christine’s embrace. Instinctively, I wanted to run right over to him – but I stopped myself from such an outward show of sibling sympathy (especially as I couldn’t instantly forgive the pain that my mother silently suffered about his absence over all those years). Instead, I slowly walked towards him, and lightly touched his arm with my hand.

‘You okay, Charlie?’ I asked quietly.

He lifted up his head. His face was tomato red, his eyes awash in tears. Suddenly he lurched towards me, his head collapsing against my shoulder, his arms clutching me as if I was a life preserver in high seas. His sobbing was now fierce, uninhibited. For a moment I stood there, arms at my side, not knowing what to do. But his grief was so profound, so total, so loud that, eventually, I simply had to put my arms around him.

It took him a good minute before his cries subsided. I stared ahead into the distance, watching Ethan (having just returned from the toilet) being gently restrained by Matt from running towards me. I winked at my son, and he repaid me with one of those hundred-watt smiles that instantly compensates for all the exhausting, endless stress that is an essential component of parenthood. Then I looked to the left of Ethan, and saw that woman again. She was standing discreetly in an adjoining plot, watching me comfort Charlie. Before she turned away (again!), I momentarily saw the intensity of her gaze. An intensity which made me wonder: how the hell does she know us?

I turned back to look at Ethan. He pulled open his mouth with two fingers and stuck out his tongue – one of the repertoire of funny faces he pulls whenever he senses I am getting far too serious for his liking. I had to stifle a laugh. Then I glanced back to where the woman was standing. But she was no longer there – and was instead walking alone down the empty graveled path that led to the front gates of the cemetery.

Charlie gulped hard as he tried to control his sobbing. I decided it was time to end the embrace, so I gently disentangled myself from his grip.

‘Are you okay now?’ I asked.

He kept his head bowed.

‘No,’ he whispered, then added: ‘I should’ve, I should’ve…’

The crying started again. I should’ve. The most agonizing, self-punitive expression in the English language. And one we all utter constantly throughout this farce called life. But Charlie was right. He should’ve. Now there was nothing he could do about it.

‘Come back to the city,’ I said. ‘We’re having some drinks and food at Mom’s apartment. You remember where it is, don’t you?’

I immediately regretted that comment, as Charlie began to sob again.

‘That was dumb,’ I said quietly. ‘I’m sorry.’

‘Not as sorry as me,’ he said between sobs. ‘Not as …’

He lost control again, his crying now ballistic. This time, I didn’t offer him solace. Instead, I turned away and saw that Meg was now hovering nearby, looking dispassionate, yet waiting to be of assistance. When I turned towards her, she nodded in the direction of Charlie and arched her eyebrows, as if to ask, ‘Want me to take over here?’ You bet. She approached her nephew, and said, ‘Come on, Charlie-boy,’ linking her arm through his, ‘let’s you and I take a little walk.’

Matt now relaxed his grip on Ethan, who ran towards me. I crouched down to scoop him up in my arms.

‘You feeling better?’ I asked.

‘The toilet was yucky,’ he said.

I turned towards my mother’s grave. The minister was still standing by the coffin. Behind him were the cemetery’s grounds-keepers. They were keeping a discreet distance from the proceedings, but I could still tell they were waiting for us to leave so they could lower her into subterranean Queens, bring out the earth movers, plug the hole, then head off to lunch … or maybe the nearest bowling alley. Life really does go on – whether you’re here or not.

The minister gave me a small telling nod, the subtext of which was: it’s time to say goodbye. Okay, Rev., have it your way. Let’s all join hands and sing.

Now it’s time to say goodbye to all our company …

M-I-C … See you real soon …

K-E-Y… Why? Because we like you …


For a nanosecond, I was back in the old family apartment on 84th Street between Broadway and Amsterdam. Six years old, home from first grade at Brearley, watching Annette, Frankie and all the Mouseketeers on our crappy Zenith black-and-white set, with the round picture tube and rabbit-ears antenna, and the imitation mahogany cabinet, and my mom staggering towards me with two Welch’s grape jelly glasses in her hand: Strawberry Kool-Aid for me, a Canadian Club highball for her.

‘How’s Mickey and his pals?’ she asked, the words slurring.

‘They’re my friends,’ I said.

She sank down next to me on the couch.

‘Are you my friend, Katie?’

I ignored the question. ‘Where’s Charlie?’

She suddenly looked hurt.

‘Mr Barclay’s,’ she said, mentioning a dancing school to which adolescent prep school boys like Charlie were dispatched, once a week, screaming.

‘Charlie hates dancing,’ I said.

‘You don’t know that,’ Mom said, throwing back half of her drink.

‘I heard him tell you,’ I said. ‘I hate dancing school. I hate you.

‘He didn’t say he hated me.’

‘He did,’ I said, and turned my attention back to the Mouseketeers.

Mom threw back the rest of her drink.

‘He didn’t say that.’

I think it’s a game.

‘Oh yes he did.’

‘You never heard him …’

I cut her off. ‘Why is my daddy in heaven?’

She went ashen. Though we’d been down this road before, I hadn’t asked about my dead father for nearly a year. But this afternoon, I had arrived home with an invitation to a Father/Daughter evening at my school.

‘Why did he have to go to heaven?’ I demanded.

‘Darling, as I told you before, he didn’t want to go to heaven. But he got sick …’

‘When can I meet him?’

Her face now betrayed despair.

‘Katie … you are my friend, aren’t you?’

‘You let me meet my daddy.’

I heard her stifle a sob. ‘I wish I could …’

‘I want him to come to school with me …’

‘Tell me, Katie, that you’re my friend.’

‘You get my daddy back from heaven.’

Her voice was weak, tiny, diminished.

‘I can’t, Katie. I…’

Then she began to cry. Pulling me close to her. Burying her head in my small shoulder. Scaring the hell out of me. And making me run out of the room, terrified.

It was the only time I ever saw her drunk. It was the only time she ever cried in front of me. It was the last time I asked her to get my father back from the celestial beyond.

Are you my friend, Katie?

I never answered her question. Because, truth be told, I never really knew the answer.


Ethan was squeezing my hand. ‘Mommy! I want to go home!’

I snapped back to Queens. And the sight of my mother’s coffin. I said, ‘Let’s first say goodbye to Grandma.’

I led Ethan forward, sensing that all eyes were on us. We approached the shiny teak coffin. Ethan knocked on it with his small fist.

‘Hello, Grandma. Goodbye, Grandma.’

I bit hard on my lip. My eyes filled up. I glanced at my father’s grave. This is it. This is it. An orphan at last.

I felt a steadying hand on my shoulder. I turned around. It was Matt. I shrugged him off. And suddenly knew: it’s me and Ethan, and no one else.

The minister gave me another of his telling glances. All right, all right, I’ll move it along.

I put my hand on the coffin. It felt cold, like a refrigerator. I pulled my hand away. So much for grand final gestures. I bit my lip yet again, and forced myself to stay controlled. I reached for my son. I led him towards the waiting car.

Matt was waiting by the door. He spoke quietly.

‘Katie, I just wanted to …’

‘I don’t want to know.’

‘All I was going to say …’

‘Do you speak English?’

‘Would you please listen …’

I started grabbing the car door. ‘No, I will not listen to you …’

Ethan tugged my sleeve. ‘Daddy said he’d take me to the IMAX movie. Can I go, Mommy?’

It was then that I realized just how shipwrecked I was.

‘We have a party …’ I heard myself saying.

‘Ethan will have a better time at the movies, don’t you think?’ Matt said.

Yeah, he would. I put my face in my hands. And felt more tired than I had ever felt in my life.

‘Please can I go, Mommy?’

I looked up at Matt. ‘What time will you have him home?’

‘I was thinking he might like to spend the night with us.’

I could see that he instantly regretted the use of that last pronoun. Matt continued talking.

‘I’ll get him to school in the morning. And he can stay the next couple of nights if you need …’

‘Fine,’ I said, cutting him off. Then I crouched down and hugged my son. And heard myself saying, ‘Are you my friend, Ethan?’

He looked at me shyly, then gave me a fast kiss on the cheek. I wanted to take that as an affirmative answer, but knew I’d be brooding about his lack of a definite response for the rest of the day… and night. And simultaneously wondering why the hell I’d asked that dumb question in the first place.

Matt was about to touch my arm, but then thought better of it.

‘Take care,’ he said, leading Ethan off.

Then I felt another hand on my shoulder. I brushed it off, as if it was a fly, saying to whoever was behind me, ‘I really can’t take any more sympathy.’

‘Then don’t take it.’

I covered my face with my hand. ‘Sorry, Meg.’

‘Say three Hail Marys, and get into the car.’

I did as ordered. Meg climbed in after me.

‘Where’s Ethan?’ she asked.

‘Spending the rest of the day with his dad.’

‘Good,’ she said. ‘I can smoke.’

While reaching into her pocket book for her Merits, she knocked on the glass partition with one hand. The driver hit a button and it slowly lowered.

‘We’re outta here, fella,’ Meg said, lighting up. She heaved a huge sigh of gratification as she inhaled.

‘Must you?’ I asked.

‘Yeah, I must.’

‘It’ll kill you.’

‘I never knew that.’

The limo pulled out on to the main cemetery drive. Meg took my hand, locking her thin, varicose fingers with mine.

‘You hanging in there, sweetheart?’ she asked.

‘I have been better, Meg.’

‘A couple more hours, this entire fucking business’ll be over. And then …’

‘I can fall apart.’

Meg shrugged. And held my hand tighter.

‘Where’s Charlie?’ I asked.

‘Taking the subway back into town.’

‘Why the hell is he doing that?’

‘It’s his idea of penance.’

‘Watching him break down like that, I actually felt sorry for him. If he’d just picked up the phone towards the end, he could have straightened out so much with Mom.’

‘No,’ Meg said. ‘He wouldn’t have straightened anything out.’

As the limo approached the gates, I caught sight of that woman again. She was walking steadily towards the cemetery entrance, moving with fluent ease for someone her age. Meg saw her as well.

‘Do you know her?’ I asked.

Her answer was a couldn’t-care-less shrug.

‘She was at Mom’s grave,’ I said. ‘And hung around during most of the prayers.’

Another shrug from Meg.

I said, ‘Probably some kook who gets her giggles loitering in cemeteries.’

She looked up as we drove by, then lowered her eyes quickly.

The limo pulled out into the main road, and turned left in the direction of Manhattan. I fell back into the seat, spent. For a moment there was silence. Then Meg poked me with her elbow.

‘So,’ she said, ‘where’s my twenty bucks?’

© 2010 Douglas Kennedy

Reading Group Guide

This reading group guide for The Pursuit of Happiness includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Douglas Kennedy. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book. 



Kate Malone stands at her mother’s coffin surrounded by the remains of her fragmented and troubled family. A mysterious woman she does not recognize stands with them, mourning quietly. Days later, this same woman demands to be in Kate’s life, explaining that she “knew her as a little girl.” Kate finally relents and allows Sara Smythe, a witty, intelligent New England woman to tell her story. Sara reveals details of her life as a young and passionate woman, being a professional writer in a man’s world after WWII, and of a secret love that bonds her to Kate’s own father, Jack Malone. What follows is a heart-wrenching, tragedy-soaked journey of a woman’s life, told to another to inspire, and teach life’s most perfect lesson, to survive at all cost, in the pursuit of happiness.


Discussion Questions

1. The novel is full of betrayals and infidelities. Both Kate Malone and Sara Smythe find these actions deplorable and are both betrayed by their significant others. However, both women find themselves wrapped up in affairs, now on the other end of the betrayal as the other woman. How do you make sense of this apparent contradiction? How can anyone who despises a certain act fall prey to the same flaw? How do they justify these actions?

2. Kate Malone reflects upon her mother’s death: “A very quiet death. Dignified. Stoic. Borne without complaint. My mother died the way she lived.” (p. 27) There is a sense of ironic anger to Kate’s statement about her mother. What is this resentment? Is she afraid she will grow up to be her? What does she want to avoid?

3. Kate Malone says directly: “You should never expect a child to make you feel wanted.” (p. 40) This statement explains Kate’s state of mind, trying to find some solace in the love from her very young child and not getting anything back. What exactly is Kate looking for when she attempts these attention-getting routines with her son Ethan?

4. Before Kate Malone receives the photo album full of pictures of her life from Sara Smythe, the mysterious woman from the funeral, Kate does everything in her power to avoid contact. Why is she so adamant about not allowing this woman to speak to her? What is this initial resistance? Where does it stem from?

5. The majority of the characters in The Pursuit of Happiness are well educated, raised with a sense of morality and religion, a strong work ethic, and exist in a middle- to upper-class lifestyle. Essentially, they are poised to live the American Dream. However, all of the characters suffer from a certain feeling of utter weariness and discontent. If modern life is about survival, success, and the accumulation of these securities, especially in Manhattan, what makes all of these characters so unhappy? What is missing from these character’s lives?

6. Kate Malone, right at the outset of the novel, is not a very happy woman. Her cynicism pervades all aspects of her life, her romantic world, her ex-husband, and her brother. The people around her never fail to remind her she’s a glutton for punishment. How responsible is Kate Malone for the overall negativity in her life? Did she have other options before her mother died to make her life better?

7. New York City is famous for the ambition, strength, and down-right hustle and bustle of its inhabitants. As Sara Smythe reflects on New York City’s skyline: “. . . it reflected the city’s spirit of arrogant indifference. It was a skyline that issued a challenge: try to conquer me. But even if you did—even if, like Eric, you were fêted as a New York success—you still didn’t ever really make your mark on the place. All that striving, all that ambition—and the moment after you’d had your moment, you were forgotten.” (pp. 361–362) Is this observation true? Is it worth it to even try? What makes characters like Sara and Eric Smythe even try to succeed in such a competitive world with barely any tangible rewards?

8. Eric Smythe’s whole career and successful life is crushed by the House Un-American Activities Committee (HUAC), an organization of the Senate during the Cold War whose job it was to root out subversive Communist propaganda in the media. They demand he turn in the names of those he was briefly affiliated with before WWII at student Communist rallies—and he refuses. He loses his job and descends into alcoholism, and eventually, death. Should he have cooperated with HUAC? How different would Eric’s outcome have been?

9. “‘Romance is a game for saps.’ . . . I had been in love with love. And I vowed never to make such a misjudgment again.” (pp. 157–158) Sara Smythe admits. Her life falls apart after not receiving any response to the heartfelt letters she had sent for months after Jack Malone went overseas. Is she justified in this feeling about romance? Was it wise to turn her back on this kind of intimacy with others? How is romance different than love? Is there a difference?

10. The novel is full of women communing through experience: broken hearts, selfish and ignorant men, the struggle for respect in the work place. What is unique to Sara Smythe’s, Aunt Meg’s, and Kate Malone’s communion through tragedy and loss? Is this form of bonding unique to women? How does it differ from men?

11. “[T]he act of admission—of owning up to a mistake, an error of judgment, a bad call—is sometimes the hardest thing imaginable. Especially when, like Jack, you suddenly find yourself cornered by a biological accident.” (pp. 293–294) Children in this novel are viewed as a trap, a burden upon individual freedom. These ideas go directly against the 1950s stereotype of the doting mother and housewife. How revolutionary are these ideas? How rare are these feelings really?

12. “Doing the right thing” is a prevalent theme within each character’s motives. Moral and religious guilt guides the decisions made by these characters. However, they still find themselves less than content. Why are the characters compelled to follow a code they no longer truly believe in? Is doing the “right thing” always the correct choice?

13. Tragedy is a constant in Sara Smythe’s life. “There is a thing called tragedy, and it shadows us all. We live in fear of it. We try to keep it at bay. But, like death, it is omnipresent. It permeates everything we do.” (p. 475) This is a bleak and honest outlook on life. How does Sara Smythe confront this? What are her methods for dealing with a tragedy that is always awaiting her? What can we learn from this?

14. Sara Smythe comes right to the edge after the death of her brother, losing her job, and losing a child. There is a moment when she has the suicide pills right next to her, a bottle by her side, and she is ready to die. But something stops her. What is this change? What drives Sara to live?

15. After Kate Malone learns Sara’s life story, she has a moment of pure clarity. She has a vision of her son, Ethan, growing up in his many different phases. She confesses to herself: “When would he realize that this is all such a deeply flawed business? That we never get it right? Most of us proceed with good intentions. We try our best. Yet so often we fail ourselves and others. What else can we do but try again? It’s the only option open to us. Trying is the way we get through the day.” (p. 572) How does Sara Smythe’s confession about her father’s past help Kate come to this realization? What was passed between these two women? What will happen to Kate? Will her world view really change?


Enhance Your Book Club

1. After WWII, the Senate created a committee dedicated to eradicating all subversive acts against the American way of life. This included harassment of homosexuals, artists, and political philosophers. Most of the people examined by this Committee never returned to their previous positions of respect. Research the devastating effects of the House Un-American Activities Committee (HUAC) on Hollywood and the Media.

2. One of the coping mechanisms Sara Smythe turns to is writing fiction. It seems that at each crucial moment of her life, it is an act of writing that saves her. Start by simply writing a paragraph a day about your thoughts, feelings, and emotions, but don’t go back and read it. After a month, open the journal again and then read through the passages. What have you learned about yourself? Can you relate to Sara’s need for self-expression?

3. The Pursuit of Happiness is a tale about Sara Smythe fighting against the banality of being a housewife and not following her dreams. She fights tooth and nail for some kind of personal freedom. Pick up Leo Tolstoy’s “The Death of Ivan Ilych,” a novella about a successful father in a middle-class society, who, when faced with a deathly illness, comes to the realization that his life has been a fraud and he is surrounded by people who do not truly love him. This could have been the fate of Sara Smythe if she had not been brave enough to break free. Compare Ivan’s failures with Sara’s triumph.


A Conversation with Douglas Kennedy

Q: Your prose is clear and precise, lyrical at necessary moments, and blunt with philosophical vigor. Who are the literary heroes you admire and what influence have these writers had on your particular style.

A: Graham Greene taught me how to write accessible novels that wrestle with life’s larger moral conundrums. Trollope taught me how to look at a historical moment of time with a novelistic sensibility—and to get all the material details absolutely right. And Flaubert taught me that quotidian life is the essential subject all writers must confront in fiction . . . because, after all, we all live (in one way or another) quotidian life. 


Q: In the late seventies, you returned to Dublin to form a cooperative theater. This led you to run the Abbey Theatre’s second house, the Peacock. Some years later, you resigned yourself to write full time. With an already established career, what made you decide to focus solely on writing? What were the risks you were taking in this decision?

A: The decision to write full time was made when I was twenty-eight years old and had just had two small plays accepted for BBC Radio. I knew I wanted to be a writer. I also knew I was still a single man with few commitments. I lived cheaply in a small studio apartment in Dublin. I continued to write plays. I wrote a ferocious amount of journalism. And little by little, I began to think that my talents lay outside writing for actors—that, verily, my future was between hard covers. But it took five years for my first book to appear. After that I moved to London and my career really began to kick-start.


Q: In April 2007, you were awarded the distinction Chevalier de l’Ordre des Arts et des Lettres, an order dedicated to the recognition of significant contributions to the arts and literature. Other notable figures who have been awarded this distinction are Jude Law, Julian Barnes, Ernesto Neto, Philip Glass, and George Clooney. How does it feel to be part of such a distinguished group?

A: I was awarded the Chevalier at a reception at the French Ambassador’s residence in London. It was so grand a setting it was a bit like being knighted at the Palace of Versailles. Of course I was flattered and honored to be made a member of such an elite club. And it’s a reminder— not that one is really necessary—that the French take writers very seriously . . . which is no bad thing!


Q: You reside part time now in Maine, but you have lived in several countries. Sara Smythe’s cottage in Maine provides solace at two crucial moments in her life, her nervous breakdown after Jack’s disappearance and after the death of her brother. What experiences at Bowdoin College and after led to your lifelong connection to the State of Maine? Does it provide you the same solace as it does for Sara?

A: I left the United States for thirty years, as my career was largely based in Europe. Of course I never stopped being American—and visited regularly. But in my imaginative mind, Maine was always omnipresent, not simply because I spent several interesting years there as a student at Bowdoin but also because I always loved its emptiness, its independent esprit, its isolation, its refusal to follow trends, and (of course) its ravishing scenic beauty—especially along its epic coastline. So, for Sara, Maine too becomes a place of refuge and consolation. If life teaches you anything, it’s that you never can run away from your problems. But, at least, in Maine you can contemplate and wrestle with them in a place of great silent grandeur.


Q: In The Pursuit of Happiness, the story is told in a confessional style, with Sara relating her life experience to Kate Malone. I was particularly reminded of Margaret Atwood’s The Handmaid’s Tale and The Diary of Anaïs Nin in the way the characters confess the story of their lives to the reader. What made you decide to use this literary technique?

A: Confessions are always so fascinating—especially if the narrator has (like Sara) a certain self-awareness and an ability to see, retrospectively, the errors that she made which, in turn, helped form the trajectory of her life. One of my favorite philosophical aphorisms comes from Kierkegaard : “Life can only be understood backwards, but it must be lived forwards.” That statement underscores all literary confessions—or, at least, the ones I write.


Q: The female characters bond as they trudge through one maddening and disappointing experience after another, and this bonding comes from telling each other stories of their lives. In what ways, would you say, is this particular style of bonding uniquely feminine? How are you able to write from the feminine perspective so well?

A: I’m always asked that question! Perhaps the answer is that I never think “as a woman”—rather as my narrator. And I see the world completely from her perspective. Perhaps a good novelist is like a good actor—someone who can slip into a role (without having to dress up!) and create an entirely convincing worldview that is so divorced from his own sensibility. Then again, all my narrators have many aspects of their creator in their complex personalities.


Q: Sara explains: “Once you grasp the flawed nature of everything— you can move forward without disappointment.” Is this a philosophy you subscribe to? That “there is a thing called tragedy, and it shadows us all”?

A: Tragedy is one of the larger prices we pay for being alive. No one ever sidesteps tragedy. It is always there, shadowing us. We don’t like admitting this, but it is a key component of human existence: the fact that life has the potential for things both wondrous and horrific.


Q: The destructive power of the House Un-American Activities Committee comes into play during the post-WWII segments in this novel. The HUAC destroys lives, displaces people, and scatters artists across the globe. What was your inspiration for writing about one of the more shameful abuses of power this country has seen?

A: McCarthyism is a dirty stain on the American body politic—and one which we sidestep at our peril, as within its vindictive machinations are all the darker aspects of our collective psyche: our willingness to point fingers, to be in thrall to the messianic ravings of an evil opportunist, to swallow all the usual tired patriotic bromides, to distrust intellectualism, to embrace conspiracy theories. Arthur Miller got it right in The Crucible when he saw the origins of these witch-hunt tendencies dating back to our theocratic, puritanical roots—and that there has always been an ongoing struggle between progressive thought and righteous doctrine throughout our history.


Q: Your novels reflect a very distinct and insightful look into American life. How has your experience living outside of the country informed your writing about the experience of living within the country?

A: Intriguingly American history was my area of specialty at college— and I briefly toyed with the idea of getting a doctorate in history. But the need to be out in the larger world sent me in a different direction. Given that, all my novels are deeply American—even if my Americanness has been shaded by a childhood in Manhattan (which the rest of the country doesn’t totally consider American!), and by thirty years in such disparate places as Dublin, London, Paris, and Berlin. But all my years abroad (and now I live part of the year in Maine) have intriguingly deepened my sense of what it is to be an American— and has given me an intriguing perspective of being the insider/ outsider.


Q: Legacy is an important theme in The Pursuit of Happiness. The legacy of one’s parents’ failures, the legacy of a heart broken by betrayal, the legacy of the death of a loved one. Kate Malone, at the end of the novel, has an almost prophetic vision of her son growing up. Kate wants to explain it all to her son, but knows she can’t, but will try. “Trying is the way we get through the day.” How close is Kate’s philosophy to your own? What legacy, as a father, do you want to leave to your children?

A: Besides curiosity—which I think an essential component of an interesting life—I would hope to pass on the idea that (as I tell my two children frequently) life is so much about persevering. You can get easily overwhelmed or defeated by life’s shortcomings or the way others let us down . . . and, more tellingly, the way we lets ourselves down. If there is an abiding theme in The Pursuit of Happiness it is the idea that you come into the world already shaped by other people’s past histories. How you then grapple with everything life throws in your path—and how your own sense of ethics dictates so much about your dealings with life’s larger questions—determines so much. “Character is destiny” is a statement (from the German poet Novalis) that so underlines my world view—both as a writer and simply a sentient person, trying to make the best of his time here.

About The Author

Photograph by Christine Ury

Douglas Kennedy is the author of eleven previous novels, including the international bestsellers The Moment and Five Days. His work has been translated into twenty-two languages, and in 2007 he received the French decoration of Chevalier de l’Ordre des Arts et des Lettres. He divides his time among London, New York, and Montreal, and has two children. Find out more at

Product Details

  • Publisher: Atria Books (October 19, 2010)
  • Length: 592 pages
  • ISBN13: 9781439199121

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Raves and Reviews

“This weighty tome is as readable as the '50s bestsellers it channels. The prolific Kennedy, known mainly in the U.K. and France, deserves a wider readership in his native United States.” —Kirkus Reviews

“Kennedy tells his epic tale with a keen eye and brisk pace.... a winningly sincere love story.” —Publishers Weekly

“Kennedy vividly depicts the heady atmosphere of post–World War II New York City, the status of working women in the 1950s, the horrors of the McCarthy era, and the ways of the heart at any time. A romantic, sweeping read that will appeal to fans of women's and historical fiction.” —Library Journal

"An engrossing novel that transcends decades.... It's a spellbinding but tragic read that you should not miss." --The Oklahoman (Oklahoma City, OK)

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