How I Blew Up—Then Rebuilt—My Life

I have a friend in recovery who says her family was blindsided when she got sober. No one had any idea; she’d hidden it well. That wasn’t my story. When I entered rehab, no one was shocked, only relieved. My drinking had stopped being private some time ago.

Nobody had been surprised when rumors about my affair surfaced long before treatment. Nearly everyone seemed to know except the one person who most needed to know: my husband. I had been sleeping with his boss, who was also mine, and the mayor of San Francisco. I had believed that getting sober would put my life back together. Instead, it left me alone with the truth.

SHATTERED PIECES “It isn’t love. It isn’t romance. It’s intoxication,” Ruby Rippey writes of the affair.Illustrator Michelle Thompson

In rehab, when the question of telling my husband comes up, my therapist leans forward—jet black hair, dark eyeliner—and delivers the recommendation of the care team. “We think it’s best for your sobriety not to tell him. Because this involves a public figure, the fallout could be devastating, and it could threaten your recovery.”

Her verdict doesn’t sit right with me. Even then, I know telling Alex is necessary.

Once home from rehab, I abandon structured recovery and try to do sobriety on my own. For months I stay dry while each day my husband goes to work for the man who had been sleeping with his wife. The silence begins to feel almost criminal.

Mixtape—1999

I first meet Alex at San Francisco City Hall during Mayor Willie L. Brown Jr.’s administration. I am the mayor’s lead scheduler; Alex directs the Office of Neighborhood Services.

For months, he finds reasons to stop by my office. A coworker tells me he’s asked about me. I say I’m not interested. Still, he keeps coming by. One afternoon he brings matzo ball soup from Max’s deli, my favorite. Another time, a mixtape.

One afternoon I am eating a salad at my desk when he walks in and sits down across from me. I look up and meet his eyes—large, brown, steady—and something shifts. I see him differently. Or perhaps I allow myself to see what was there all along. He carries himself with an effortless assurance. There is gravity to him.

On New Year’s Eve, as time clicks to 2000, we kiss for the first time on a friend’s back porch. We are pressed against the wall as midnight erupts across the city. Fireworks, car horns, the collective exhale of a century ending. It feels like a beginning. After that night, I play the mixtape on repeat.

The Supervisor—2003

As Brown terms out, my new husband and I are recruited to join the next mayoral campaign. A young supervisor from District Two enters the race, often described as Kennedy-esque. Alex is field director; I am deputy finance director.

We move through those months side by side, through my pregnancy, through long stretches when victory feels uncertain. When our candidate wins with 53 percent of the vote, we walk into City Hall together. We are convinced we are building something new.

Beneath the Dome—2004

A year into the administration, the city still carrying the energy of a political dawn—a mayor whose charisma seems to gather momentum.

Just a month after taking office, he legalizes same-sex marriage. When it happens, I am seven months pregnant. I stand beneath the dome of City Hall in a maternity wrap dress and leopard kitten heels, deputized to marry couples.

The administration is settling into itself. I serve as commission secretary, coordinating appointments to nearly a hundred city boards and commissions. Down the hall is my husband’s office—the deputy chief of staff. Some mornings I bring him two hard-boiled eggs in a Tupperware container. He looks up from his desk and smiles at me.

One day I am told my office has been reassigned. The mayor wants me at the desk outside his door, a gatekeeper. I understand the logic. It’s a new administration full of young staffers improvising their way through it. Still, losing my office feels like a demotion.

But my new desk quickly becomes a nerve center. I manage the steady stream of people who want something from him, and I pass notes on thick yellow index cards, a holdover from Brown.

One night, we all meet at a Mexican restaurant on Lombard Street. Warm tortilla chips. Limes. Margaritas sweating in glasses. As the waiter takes orders, I feel the mayor looking at me. I glance up—across the table—back at him. As if caught off guard, he reacts, pointing at me.

“Hey—you look really good,” he says. “You’ve lost all your pregnancy weight.” There’s an awkward laugh. I reach for another chip and stare at my husband’s margarita, the salt rim catching the light.

I want it.

But I’m in another self-enforced stretch of sobriety, so I sit on my hands and wait it out.

After that, I start paying closer attention to what I wear. Chanel makeup. A yellow silk dress fitted at the waist. Pink patent leather heels. At senior staff meetings, we sit in a semicircle facing his enormous oak desk, 12-foot velvet curtains drawn tight, casting the room in a private glow. I wear my new heels. A tight pencil skirt. I cross my legs; I feel important.

It’s hard to reconcile that woman with the person I would become in one short year. My self-willed stints of sobriety grow fewer and farther between. Until they stop altogether.

The White Dress—July 2, 2005

If there’s a place it starts, it’s at an afternoon wedding over Fourth of July weekend. A longtime City Hall staffer is getting married. Everyone is going. I wear a white strapless dress; my mother says it isn’t appropriate for a wedding. She urges me to wear a tan wide-brimmed hat to add color, but I leave it in the car.

The reception is at a Napa Valley estate, surrounded by vineyards. Long tables sit in the afternoon sun. Alex and I stand with a group of staffers—talking, laughing, Champagne in hand. I am restless in a way I can’t name. I drink Champagne, then wine. Then more wine. My dinner goes untouched.

My boss and I end up in the narrow hallway outside the bathroom at the same time. We wait, across from each other. The space is tight. The silence stretches. He slips his hands into his tan trouser pockets and smiles—his usual shy, aw-shucks smile. I say nothing. I hold his gaze longer than I should.

The air changes.

By the time night falls, I am sitting on the edge of a hot tub with my feet in the water. He is across from me, slipping off his shoes and socks, rolling up his pant legs. My husband leaves soon after, irritated that I want to keep partying while he drives home to our one-year-old son.

The next clear memory is getting into the back of my boss’s chauffeured town car, heading to The Carneros Inn. There are others—his sister, a few more. The car smells like new leather. I stretch my legs across the center console and let my heels fall off. He is in the front seat. He takes one of my feet and begins to massage it, the gesture half-hidden inside the loud car.

Then nothing.

I wake the next morning beside him, still dressed. I am cold, almost shivering, and my dress—the one my mother warned me not to wear—is soaked from the waist down. I had passed out. I had also wet the bed. (It wasn’t the first time.)

He is still asleep. I find my clutch, gather my heels, and leave quickly, wanting to get back to Alex.

A few days later, back at work, my boss slips my gold bracelet onto my desk as he passes. A gift from my grandmother, left behind in the Napa hotel room. He keeps walking. We pretend nothing has changed.

But everything has.

The boundaries begin to disintegrate. I linger in doorways, position myself within his sight line. At events, he holds the doors, waiting for me to pass first. The texts shift from work to something else. I manufacture reasons to be near him. The choreography becomes obvious. People notice.

As the performance unfolds in plain sight, I start measuring my days by how close it is to five—when I can start drinking. I scan his calendar for openings, places I might “happen” to see him later that night. I arrive, make sure I’m seen, then leave.

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My phone lights up soon after. “Where are you?” But it never matters where I am because I always go to him—his penthouse in Russian Hill, a private back room in a North Beach bar, the W Hotel in Los Angeles.

We meet and we drink. There is sex, but it isn’t the point. The point is proximity—to power, to being chosen, to feeling newly visible—no longer muted by pregnancy, by new motherhood, by the strain of white-knuckling long stretches of sobriety.

It isn’t love. It isn’t romance. It’s intoxication. The text message is a hit. The glance across the hallway, a hit. The risk floods my bloodstream. I walk down the corridors of City Hall—my nude stilettos striking the marble floor. He looks at me, his gaze deliberate, newly curious. It feels like oxygen.

I don’t stop to consider the consequences—not for Alex, not for myself, not for the life I am building. I am responding to the feeling. His attention lands like a high, and I follow it with a single-minded devotion.

The Stain

When I ride with him to his penthouse in Russian Hill, the driver is told to wait. I protest. But in the early hours of the morning, when I make my way back onto the sidewalk, the black Lincoln is still there, idling at the curb. I slide into the back seat, thanking the driver too profusely, humiliated by the certainty that he knows.

One night at his place, I am in his king-size bed, lying on my side, watching him. He is on all fours near the edge of the bed, scrubbing furiously at the carpet with a washcloth. I’ve knocked over a glass of red wine. It blooms across the pale rug. I remember thinking: That stain isn’t coming out. As if he can hear me, he looks up, frustrated. “You know, we really can’t do this anymore. You can’t be doing this to Alex.”

Later, alone in the back seat of his chauffeured car, I feel a sense of relief. It reminds me of my second DUI, over a decade ago—before Alex, before City Hall. Red and blue lights flashing in my rearview mirror as I came off the Golden Gate Bridge. I remember thinking, Maybe now it’s over.

But the encounters continue, on and off, for months. I come home at three in the morning, wasted, breath thick with alcohol, and slide into bed beside my sleeping husband, pressing my cold body against his for warmth. The familiar fear floods in.

Some mornings I lie in bed, hungover and hurting, and plead with Alex: Please don’t let me drink tonight. It’s an impossible request. He can’t control it any more than I can. “Can’t you just stick to two glasses of Chardonnay?” he asks.

I love him for his stubborn refusal to see the full ruin of me, his belief that moderation is a skill I might someday learn. I love the version of myself reflected in his eyes.

Tiny Buttons

I plan a girls trip to Los Angeles, knowing he will be there for work. By two in the afternoon my friend and I are drinking chilled Chardonnay at the Maison 140 pool in Beverly Hills. My phone buzzes. He’s at the W Hotel. “You guys should come by.” We polish off our wine and head over.

At the hotel bar, I remember only flashes—leaning in too close, laughter pitched too high. Then it goes black.

I wake beside him the next morning. The room is quiet. My head pounds. On the floor near the bed are tiny shirt buttons scattered like coins. Not mine. One is stuck to the back of my thigh. I peel it off and dress carefully, leaving without waking him.

Back at my hotel, I tell my friend I need to cut the trip short. I invent something about my son and book the first flight home. On the plane, with an empty seat beside me, I cry for the first time—a steady, stunned grief. I am overcome with the understanding that the consequences will not end with me. They may cost me the best thing that has ever happened to me: Alex. But worse, they will fall hardest on him—the person who least deserves them.

When I land, my phone lights up: “Thank God the W had T-shirts.” Only then do I understand—hazily—that I tore his shirt off, every button ripped loose.

By now, the version of myself manning the nerve center is collapsing. I am now working in a makeshift office that used to be a copy room. I am coming in late, hungover most days. Leaving early, thinking only about drinking.

The Pill

As my drinking and my life begin to spiral, I turn to Antabuse, a pill that promises to make me ill if I drink. Each morning I swallow it, certain this will be the day I hold the line. By late afternoon, my resolve thins, and I begin bargaining with a future version of myself.

One night I make it until 7:30. At a private party, trays of Chardonnay circle the room. I watch them pass as if they are carrying relief. I take one. Then another. Within minutes, my face turns red and swells. My eyelids become slits. People stare. “Ruby, your face—what happened?” I wave a hand. It’s just the lights. They’re so bright.

The pill makes me ill. But it doesn’t make me stop—it just makes me stop taking it.

So I turn to cocaine.

Alone, cocaine doesn’t appeal much to me. But after one or two bottles of wine, it makes it so I can drink twice as much for twice as long.

The nights blur: rooftop bars, wine, cigarettes, and names I immediately forget. Strangers’ living rooms. Finishing the last lines long after I stop wanting them. The taxi ride home as the sun comes up. The city already moving—belonging to people who have slept. My body, a crime scene.

People ask how Alex didn’t know—why he didn’t ask questions when I was stumbling home at three in the morning. My sister, who witnessed my deterioration up close, says that Alex and I were both having an affair with the mayor. He was so devoted to his job—and boss—that he chose not to see what was happening in front of him.

By now, my single-minded devotion has shifted: The drink and drug have taken its place. I move from bar to bar, staying out until dawn with people who don’t ask questions. When his texts light up my phone—urgent, insistent—I feel nothing.

My sister begins trailing me at night, trying to keep me in sight. One morning, just after five, she drives me to the emergency room. My nose won’t stop bleeding—again. I press an old T-shirt against my face and watch it darken. My jeans hang loose. Her hands tighten on the steering wheel.

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The doctor cauterizes the inside of my nostril. The smell of something burning—metallic, bitter—fills the small exam room. On the drive home, as the sky begins to lighten, my sister tells me she’s spoken with our father. I stare out the window. She says, “He’ll pay for rehab—if you’ll go.”

The sentence lands harder than anything I did all night. Until then, I had believed this was a private failing, a defect in discipline. I had been trying to hold together a job, a marriage, a baby, and an affair while drinking and using cocaine. For the first time, stopping felt possible. I look at her and say: Okay.

Wickenburg—May 19, 2006

The next morning, I fly to Arizona and check into a treatment center. I stay for seven weeks.

While there, I write two letters to my boss: one official, one private. In the first, I resign—knowing that if I am to stay sober, I cannot return to City Hall. In the second, I end the affair.

What I didn’t know until later was that my sister had also reached out to my boss. She called his cell and told him not to see me again. “She is unwell. She is getting help. Even if she reaches out to you, it is your responsibility to say no.” His response, she told me, was some version of “God bless, God bless.…”

My family placed much of the blame on my boss and the conditions of the office. But it wasn’t the affair that derailed me. It was my alcoholism. The affair just gave it somewhere to live.

When I return home from rehab nearly two months later, I try to resume life as a wife and mother. Meanwhile, Alex leaves each morning for City Hall—for the man I have betrayed him with, still unaware of what had happened between us.

Soon he is recruited to manage the mayor’s reelection campaign. His hours stretch into strategy sessions and dinners that run past midnight. Brick by brick, he is building something.

For months, I say nothing. The silence settles into my body like a fever. Until one night I am no longer able to carry it.

Confession—January 13, 2007

Alex is home in San Francisco with our son, handling bath and bedtime. I am at my parents’ house in Napa. I sit downstairs on the living room couch in the dark, lit only by the glow of my phone.

I begin drafting an email, my thumbs moving quickly. I keep it plain: just sex—on and off for months—with the mayor. It ended before rehab. I’m sorry. I blame my alcoholism. I stare at the screen for a moment, then press send and turn off my phone.

In the morning, I drive straight back home. When I walk through the door, the house looks the same. Toys on the floor. A bottle in the sink. But Alex is not the same. He is standing in the kitchen. His face is drained of color. He looks at me in a way I do not recognize.

His voice is careful, measured—one of the qualities I have always loved about him. Even in catastrophe, he remains unflappable. He says he needs a few weeks to think. Then he packs a bag and leaves.

I still wonder which was the greater offense: my infidelity or my failure to look him in the eye when I told him about it.

During that time, he requests a meeting with the mayor, who is still in Davos at the World Economic Forum. Word has already reached him in Switzerland that I might have confessed. All day, his number flashes across my phone.

The meeting is set for the day after his return from Europe. Alex makes the drive to City Hall, a drive he’s made thousands of times. For years, he answered late-night calls from his boss, sacrificed weekends without hesitation. He wants to hear it directly—to look him in the eye one last time. There is no straight answer.

Above the Fold—February 1, 2007

By morning, my face is above the fold in every local newspaper. SFGate: “Campaign manager resigns—confronts mayor, who is ‘in shock.’ ” The New York Times: “San Francisco Mayor Admits He Had Affair with Aide’s Wife.” Television stations run the story on a loop. The mayor holds a press conference live on TV. “Everything you’ve heard and read is true,” he says.

I watch from my parents’ house in Napa. I sit on the pale green chenille couch, ashen and silent. My family moves around me, talking strategy. My father offers to get Cold Stone Creamery since I haven’t eaten in two days. My mother scrolls through the readers’ comments about me online. My brothers alternate between inappropriate jokes and threats of revenge.

My phone floods with calls and texts from reporters. I don’t answer. I don’t respond. I say nothing. I wait out the weeks until I can see Alex again. The headlines, the commentary—none of it matters. I think only about him.

Bad News

It is a Sunday morning. I am having coffee with a friend at an outdoor café in Noe Valley. On the abandoned table next to us lies the San Francisco Chronicle, featuring a profile of the mayor’s new girlfriend. My friend picks it up and begins reading aloud.

“I shouldn’t say this, but…if people did research into the scandal…the woman is the culprit.”

I have seen commentary about myself before—speculation, condemnation, the occasional defense. That is not new. What is new is his girlfriend entering the record—someone who came into his life after the affair.

The next morning, the same friend texts me a link to SFist.com. I click. I scroll. My heart begins to race, then everything slows. My mouth goes dry. She has more to say.

“I’m a total woman’s woman, girls girl…what’s your definition of affair?…it was a few nothing incidents when she showed up passed out outside of his door…she is bad news.”

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I read the sentences twice. They do not change. Bad news. A few nothing incidents. A thin, hollow feeling opens in my chest.

A columnist from the San Francisco Examiner calls. I know him socially. He asks if I want to speak publicly. I thank him but decline. He says her framing makes it sound nonconsensual. It wasn’t, I tell him. I was not coerced. I knew what I was doing.

#MeToo is still more than a decade away, but the arguments are already forming. I hear every explanation. None absolves me. Yes, the drinking mattered. So did my arrogance—the belief that consequences were for other people.

I was not confused or naive. I was a grown woman who made choices that hurt someone I loved.

I am the culprit.

A Real Girl’s Girl

Soon after, Kamala Harris calls. I know her from the Brown administration; she is now the district attorney. I tell her people are urging me to speak publicly. A publisher has offered an advance for a memoir. I am broke and unemployable.

She listens, then says simply: “I wouldn’t say anything right now, Ruby. Just pause. More time will give you better perspective.”

It turns out to be the best advice I receive. I am newly sober and still inside the wreckage—unable to make sense of anything, let alone speak clearly about it.

So I stay silent.

Alex

I believe there is a possibility he will take me back; that somehow honesty will stabilize things. He will be furious, wounded, but we will absorb this and move forward. I am wrong.

Since my confession, Alex and I never sleep under the same roof again. Living with my drinking required constant effort from Alex: emergencies, quiet cover-ups, extra parenting. My confession changed the equation. Whatever hope he still carried about who I might become had to give way to who I had been.

Reading his emails to me from that time is the hardest part to revisit. Not because of what he says, but because I can see the result of my actions landing on the person I loved most. The distance between what I felt for him and what I did to him is difficult to hold.

In those messages, he is never cruel or vindictive. He is trying to understand how his life could be upended by the person he trusted most.

He tells me he can’t sleep, that he lies awake trying to make sense of it. The damage, he says, isn’t contained to our marriage. It moves outward into everything: his work, his future, his financial situation, his sense of himself—the life he thought he was building.

In those first months, I cycle through apologies, long emotional explanations, attempts to reach him. Later, in recovery, I learn a different way to respond. Not with words but with restraint.

To leave him alone. To make his life easier where I can and not add to what I have already broken—even if that means never being let back into his life again.

The greatest cost was never public. It was what I did to a good man who deserved better than I gave him.

Both Things Are True

Eleven years later, #MeToo arrived with a new version of my story—one in which I was not the culprit but a powerless subordinate. I pushed back. Claiming responsibility felt like the last form of agency I had.

Still, the reckoning exposed what I had missed: Power does not need to coerce. It only needs to exist. The responsibility to hold the line belongs to the one who holds it. That didn’t happen. But I didn’t stumble into the space left open—I saw a possibility and went for it.

Both things are true: I am responsible for what I did. Power does not distribute consequences evenly.

Protection—January 29, 2026

I wake to a voicemail from someone I know from my City Hall days, now an adviser to my former boss. “Hey Ruby! Blast from the past. Give me a call.”

Later, on my way to yoga, I pull over and call him back. After a few minutes of small talk, he gets to the point. “The governor’s memoir is coming out in a few weeks,” he says. “He wanted you to know—you appear in a few pages.”

I pause.

“Would you like me to read them to you? There’s nothing bad at all—nothing to worry about.”

“No thanks,” I say. Then I add, “Does he tell the truth?”

With a small, uncomfortable laugh, he says, “Well, we all remember things differently, don’t we, Ruby?”

For my former boss, it is a footnote in a longer arc of ascent. For me, it is the fracture that split my life into before and after.

When I read the pages a few days later, a familiar feeling returns, the one of being written about by someone who assumes I won’t answer. He describes it as “the briefest of affairs.” His sister, he notes, observed that I was “hanging a bit too close.”

He also writes that he was the one who “came clean” to Alex. That detail—subtle but significant—is the one that stays with me. It reads—to me, at least—as a version of events that gives him credit for something I had already done. Technically defensible, perhaps, but one that leaves the unmistakable impression that he, not I, was the one who told Alex the truth.

But resentment is a luxury I can’t afford. Instead, I return to gratitude, not for the affair, not for the pain I caused Alex, but for the totality of what followed. I required something catastrophic to change direction. Something that made the cost of going back—of drinking again—unthinkable.

The pain of what I did to Alex, and to myself, has stayed with me every day for two decades. I used to think that was punishment. Now I understand it as protection.

What Remains

Today I am 20 years sober.

I traded City Hall galas for church basements. Stilettos for New Balances. I met Ryan and built a second marriage—one that has lasted longer than the first. His steadiness has changed my life. Together we’ve built the kind of family I wasn’t sure I’d ever have. We are raising our 11-year-old son together.

It took more than a decade for Alex to look me in the eye again. We co-parented without hostility, but he kept his distance. I focused on what I could: staying sober, showing up for our son, living differently.

Eventually, small openings appeared—iced teas at The Depot with our son, groceries dropped off during COVID, dinner for our son’s birthday. When he got engaged to Heidi, a close friend of mine, the gatherings became more frequent.

Then last year, I was driving home one afternoon when he called. We slipped easily into conversation, laughing about something small involving our son. Then his tone shifted.

“I actually called for another reason,” he said. “Heidi and I want you and Ryan to come to our wedding in November.” The words hung there between us. After a moment, he filled the silence. “Ruby. We are family.”

And so we went.

My husband and I sat among the guests as people stood to toast the couple—Alex laughing, raising his glass. Then our son stood up, grown and composed, and gave the best man’s speech. Ryan’s arm tightened around me; I leaned into him. Alex caught my eye and smiled.

We lost the marriage. We didn’t lose the ability to become another version of a family. The damage was mine. But so is the life rebuilt in its wake.

Hair products by Kenra Professional; makeup products by Charlotte Tilbury; hair and makeup, Lee Stewart. For details, go to VF.com/credits.