Edited by Kevin Allison

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A “fascinating” (MetroSource) collection of uncensored, confessional, and at times outrageously funny essays about coming of age, coming out, and the wildest experiences that define us.

Collecting the most celebrated stories from the hit podcast RISK!, along with all-new true tales about explosive secrets and off-the-wall adventures, this book paints a spellbinding portrait of the transformational moments we experience in life but rarely talk about. No topics are off-limits in RISK!, no memories too revealing to share. From accidentally harboring a teen fugitive to being poisoned while tripping on LSD in the Mayan ruins, these stories transport readers into uncharted territory and show how your life can change when you take an extraordinary leap.

In these jaw-dropping stories, edited and introduced by RISK! host Kevin Allison, writers reveal how they pushed drugs for a Mexican cartel only to end up kidnapped and nearly killed, how they joined a terrifying male-empowerment cult and fought desperately for a way out, how they struggled with pregnancy complications and found a hero where they least expected it, and so much more. A lifelong construction worker shares the intimate details of transitioning to being a woman, a bestselling author discusses how he assumed the identity of his babysitter online in a social experiment gone awry, and a beloved comedian discusses how a blow job from a prostitute changed his life. By turns cautionary and inspiring, RISK! presents an extraordinary panorama of the breadth of human experience and a stunning tribute to the power of the truth to set us free.

Introduction

You have a story you've never dared to share.

Maybe it's about that bewildering night you lost your virginity. Or the fistfight you hate to admit that you started. Or the week your dad died and you learned a creepy secret.

Maybe you have told a version of this story before—to your therapist or your spouse. But you cleaned it up a bit. You left one stone unturned. It could be you were tempted to spill the whole messy truth to your closest friend one night over drinks, but that scolding voice in your head said, "Hey now. Some things are better left unsaid."

But what if I told you there's an extraordinary place where you'd be celebrated for biting the bullet and sharing the whole damn truth—the good, the bad, and especially the ugly of it—with the world?

Hello kids, this is RISK! That's exactly what we're about.

If you're one of the millions of people who have heard the RISK! podcast or attended one of our live shows, you already know the motto we've lived by for more than eight years and 350 episodes. "RISK! is the show where people tell true stories they never thought they'd dare to share." We say that on RISK!, nothing is inappropriate until something just…is. But then we talk about it anyway! Because unlike other storytelling shows, RISK! doesn't censor our contributors' stories to suit the standards of family-friendly radio. Nothing is too emotional, too graphic, too strange.

I have collected in this book some of my favorite stories of unforgettable life experiences courageously shared on the podcast, as well as extraordinary new stories that have never been told anywhere. What ties them together is how surprising, gripping, and nakedly honest they all are. I tell people that RISK! is soul food, served spicy. Prepare for stories that will make you laugh and cry…and that may keep you up at night.

Our live show happens once a month in New York and LA, but I also take the show on the road. After each event, people line up to give the storytellers and me a hug and share something. A college kid in St. Louis had tears streaming down his face when he told me the podcast saved his life. A man once emailed to say getting his stepson to listen to a RISK! story helped the two of them to finally relate to each another and moved the boy to get help for his drug problem. A college student emailed to say the show helped her come to terms with her rape. After listening to RISK!, she knew how to get help. At a show in Austin, an older married couple told me they'd been on the verge of divorce, but then came out to each other as "kinky" after hearing an X-rated story on RISK!, and it saved their marriage.

These amazing shifts that happen to people—these transformations—are just as powerful on the page as on the podcast. They're what happens when we see true courage in action and are inspired to take a risk ourselves. All the brave storytellers in this collection bare not only their souls but also some of their darkest secrets.

I can attest to how unfiltered honesty saves lives. It saved mine.

Picture this. At five years old, I began to be terrified of myself.

I was a bucktoothed redhead, usually "bouncing off the walls," as my mom said. It was the messy mid-seventies, and we were as Catholic as they come in an oh-so-Republican part of Ohio. At that age, I'd never heard of "having a crush" on someone. But I realized that I felt something for Sammy Buchanan. He was born the same day I was, lived a few houses down, and we were the best of friends. Sammy had sandy hair, a sunny smile, and an amazing toy collection. One rainy afternoon, listening to the cartoon mice chirping on the Disney Cinderella LP, I blurted out, "Sammy! Wouldn't it be funny if we took off all our clothes?!"

I was right—it was hilarious! We ripped off our clothes and laughed up a storm. Romping around, some part of my little brain knew exactly why I'd made the suggestion—that for me this was more than just humorous. Suddenly, Sammy's eyes were wide as quarters and he said, "What's that?!"

He was pointing at my penis. I looked down and my jaw dropped. It was doing something both of us found bewildering—it had turned stiff and was pointing toward the ceiling. I instinctively knew this was an outward sign that I found this boy-and-boy nakedness exciting.

Sammy laughed it off, but I couldn't. I remembered something his older brother, Rick, had told the two of us just days earlier. "When people say gay or fag," he'd said, "they mean a boy who likes other boys the way that a boy is supposed to like girls. That's why it also means 'disgusting' and 'lame.'" I felt hot and cold with fear. "In one year, I have to go to kindergarten," I thought. "I'm going to meet so many kids. What if one of them finds out I'm a gay fag?"

Most gay kids aren't self-aware so soon, but I was a precocious (and horny) little guy. Because I forced myself not to be honest with anyone around me, a black cloud of anxiety hung over my head everywhere I went throughout my childhood. I was obsessed with keeping my sexuality hidden.

But by my teens, I got gutsy, fascinated by the idea of coming out. A little over a decade after the Sammy Buchanan incident, I finally mustered the courage to share about my sexuality with friends and family members, one by one. I felt a gush of relief and affirmation each time. Those relationships only deepened from my sharing the truth. I've spent my whole life learning the essential lesson that each of the writers in this collection live out.

But it wasn't just my sexuality that was different. Family members told me I was too expressive. Friends told me my sense of humor was too strange. Teachers told me my voice was too big. I felt like a freak most of the time. For a few years after college, I was lucky enough to be in a sketch comedy group called The State with a series on MTV, where it was okay to be too much this or too much that. But when I changed my focus to doing solo character monologues after The State broke up in '96, I was drowning in self-consciousness about what Hollywood casting directors might think of me. I did all I could to avoid seeming too loud and gay, too Midwestern and polite, too goofy and surreal, or too serious and spiritual. In an effort to not be too much of anything, I had let myself become nothing. No one would hire me. I was a wreck, and I was starving.

Everything changed one January night in 2009. I was about to turn forty. I was twelve years away from my successful period on TV, and twelve years into drinking myself silly and thinking of jumping off the Williamsburg Bridge. I did not want to head into another decade in this rut, but on this January night, I did a solo show of character monologues at San Francisco Sketchfest, and everything that could go wrong did. The show was called F*** Up (about five guys who had f***ed up their careers!) and on that night, it lived up to its name.

A fellow State member, Michael Ian Black—whose amazing story "The Ring of Fire" I've included in this collection—was there. After the show, I asked him what he thought.

He paused, then said, "I think everyone in that audience tonight would have been more interested if you'd been sharing your real-life experiences. Why not just drop the mask and tell us the truth?"

I felt a sting of nervousness. I said, "Ugh. Putting myself out there like that, with all these odd contradictions that make up who I am, it feels too risky!"

He stopped walking and said, "If it feels like a risk, it's because you're opening up to the audience. But then they will open up to you."

It was one of the most important things anyone has ever said to me.

On the plane ride home, I promised myself I would tell the boldest true story I could think of onstage once I was back in New York. I'd heard of true storytelling shows but had never been to one. A friend told me that Margot Leitman and Giulia Rozzi hosted a show called Stripped Stories at the UCB Theatre in Chelsea featuring tales from people's sex lives, so I called them.

"I can tell the story," I told Margot, "about the first time I tried prostituting myself and failed, when I was twenty-three. It was a comedy of errors." She said, "Not only can you, you must!"

But when the day of the show came around, I felt like a frayed power line. Just a few hours before showtime, I called Margot to back out. "It feels too risky," I told her.

She said, "Oh wow! That's so great to hear!"

I was confused, but her laughter put me at ease. "Listen," she said, "there are still tons of taboos around talking about sex! So when one of my storytellers calls me the day of the show and tells me it feels too risky—and someone often does—I know that if I can just talk them into going through with it anyway, that will be the story that ends up meaning the most to the audience."

I had to do it.

That night, I told the story (later featured on RISK! Episode #451) called "The Hustler." As I was telling the story, I felt a voice in the back of my head saying, "Do I sound too gay?" and "Was that part too goofy?" and "Shit! I definitely sound too Midwestern here.…" But eventually, I stopped focusing on that voice and started to notice something else. For the first time, I wasn't reciting a memorized monologue at the audience. I was conversing with them. Their eyes weren't just lighting up from the laugh lines; they shone with compassion and recognition. This flow of energy between myself and the audience was new to me. The more intimate I got with my revelations, the more they leaned forward. Afterward, people didn't just tell me I was funny; they offered their own truths and memories. I'd reached them, contradictions and all. I'd turned a corner.

I walked away from the UCB Theatre buzzing with excitement. What to do next clicked into place: I would create RISK!, a storytelling show where people could come out about anything, no matter how outrageous or emotional or scary, no matter how funny or strange. It would be a place where people could share the most meaningful moments from their lives with as much vulnerability as they'd show with their therapists.

In your hands, you hold the most stunning tales of adventure and wonder that emerged from this vision. These are stories about coming to terms with who we are, living our best lives and facing death, walking out of the house intending to murder a bully before your friend talks you out of it, being bitten by scorpions atop an isolated mountain, and getting a life-changing insight from the eccentric uncle from whom you least expect it.

Each of these stories will change you in a different way. If you let them, they might inspire you to come clean in ways you never imagined you would. Remember that story you thought you'd never dare to share? As I say at the end of the podcast each week, "Folks, today's the day. Take a risk!"

—Kevin Allison

Bad Samaritans

A. J. Jacobs

With Great Beauty

My wife and I have kids, and a few years ago we hired a babysitter. In our particular case, the babysitter happens to be crazy hot. Her name is Michelle, she's twenty-seven years old, and she looks like Angelina Jolie but without the freakish lips.

Beyond being a great babysitter and an unusually attractive person, Michelle is a lovely, kind woman. But since for some reason she's single, we wanted to see if we could find her a good boyfriend. So one day we sat her down and we said, "Listen, can we set you up on match.com? How about that?"

She was tentative. "It's a lot of creeps on there," she said, "and I'm not really a writer."

But I told her, "Listen, I'm a writer. I'll write the emails for you. No problem!" It seemed like a good idea. "I'll be sort of the gatekeeper," I said. "I'll email these guys and weed out the creeps and I'll help you, you know, just go out for a latte with the nice guys."

"Okay," she said. "I guess so…"

We set up an account. I put up some pictures of Michelle, and within a minute my computer goes "Bing!" I've got a page view! Then my computer goes "Bing, bing, bing, bing, bing, bing!" Suddenly, I'm very excited. The emails start coming in. That first night, I get like a dozen. They look like you'd expect: "You are so beautiful"; "I love your smile"; etc. When I read those, I'm no longer just excited; I'm exhilarated. Because I've never had this much positive feedback in my life. And, yes, I realize it's technically not for me, but still, it's an incredible thrill.

I find that there are some potential good guys, but there are also a tremendous number of guys that I have to weed out. As I start to read through them, more emails come in, and I realize that there will soon be so many that I have to start coming up with a system. So I make a list of the deal breakers. If there's a guy who mentions the word ladies in his opening email, I figure that's not good. If he says that his best feature (the website asks you your best feature) is "Ass" or "Butt," even if it's ironic, that's a strong red flag. If the guy's head is tilted more than twenty degrees—to the right or the left; there's no right way to tilt as far as I'm concerned—then he's out.

There was one other deal breaker. If the guy mentions female anatomy in the first email—for example this one man opened with, "I'm not a professional gynecologist, but I'd be happy to take a look"—that's an easy no.

You'd be shocked by how many of these guys there are, and though I try to send notes to all of them to let them know I'm not interested, I find there are too many to write to them all. But I find this one guy, his user name was "Sexy Gentleman," and I said to myself, "Michelle should really respond to this guy." I thought this would be a nice thing for Michelle to do. So I sent him a note saying, "You seem nice. I don't think we're right for each other, but just FYI, you might wanna rethink 'Sexy Gentleman' as a screen name. It might be, for some women, a little too on the nose. You know?"

I felt like I was helping people. This incredible feeling rushed through me. I could help the creeps overcome their creepiness and also find some great dates for our hot babysitter. And there were certainly a few guys that I liked. There was this music teacher with long hair, and he was very humble and sweet, and he wrote these long, funny emails about xylophones. I took him to Michelle and said, "What do you think?"

"Alright," she said. "I'll meet him."

So they have a date at the Mexican restaurant. I don't go to spy, even though I really want to. When she comes back, I ask her to tell me everything, and she's like, "Yeah, I liked him. I think I liked him. He was cool, sweet. I'll go on a second date." And I'm like, "Yes!" Because I am living vicariously through her, and also through him—through both of them.

I was relieved, too, because this was her first date I'd set up and my personality—her online personality, that is—is a little bolder than her real personality, which I warned her about. But she told me that she changed her personality at the restaurant to try to fit into her online one. She tells me that when he walked in, she made him turn around to check out his butt.

I was learning quickly that it's very powerful—for me it's a rush—being a hot woman. For instance, I got this other email from this guy whose opening essay started, "When I was a child, I witnessed a clown jump to his death from a seven-story building, and it was the only time a clown has made me laugh." Obviously, I was disturbed, and so I wrote him back, saying, "You know, you seem nice. You're very funny. But you're a little dark for a sweet girl like me." Then when I look at his profile the next day he's changed his opening essay completely. Now it's all about Care Bears and snuggling and rainbows. He writes me that day saying, "I need a sweet girl. I like you." I felt a pang of compassion for this bizarre, creepy man. But I couldn't bear to reach back out and set something up—I couldn't do that to Michelle.

The sleazeballs continued apace, dozens of new ones every day. This one guy who looked like John Turturro opened with the line, "You seem like a handful." To that, my only response was silence.

A few months before all this, I had read in the course of my work for Esquire magazine a book about pickup artists, and one of the strategies they use as an opening line is to mildly insult the woman. The idea is to lower her self-esteem, and then she'll wonder if maybe this pickup guy talking to her is better than she is, and maybe she sort of sucks. The term for that is negging, as in saying something negative, and as the book about pickup artists came back to me, I realized this guy had just negged me. So I wrote him back, saying, "Hey, have you ever read the book The Game by Neil Strauss?" He writes back, "Why do you ask?" And I'm like, "I just busted your ass. I knew it." Because I knew that if he hadn't read The Game, he would have said, "No, I don't know what you're talking about."

After some back-and-forth I finally got him to confess that he's a part of this pickup artist community. He knew all these other guys who subscribed to the philosophy. When I find this out, I get quite angry. "This is not a game! I am looking for a boyfriend or a husband. Stop toying with my emotions!"

I was like Susan B. Anthony, and I just wasn't gonna take it.

Soon, I found another guy who I really liked, a scientist who seemed very sweet, though he had ears sort of like Prince Charles'. I asked Michelle, "What do you think?" And she said, "Yeah, let's try it."

We make a date. When Michelle comes back from it, I ask her about everything, and she tells me he never showed up. "He blew me off," she said. "I'm out. I can't do this anymore." I could tell she'd been crying. "You know," she said, "this is too…" but she didn't finish the thought.

I thought, "What the fuck is wrong with this guy?"

The next day, the guy emails me. He was at the Starbucks. He was outside and she was inside. "Sheesh," I think. "Kids today. They can't even find each other in a Starbucks!"

Next I get my favorite email yet. This guy whose screen name is "Watch Me on TV" and who doesn't have a picture reaches out. "Who is this?" I wonder. "Al Roker?" I open the email and it says this: "I'm married, but I'm looking for a girl on the side, and I wondered if you could be that girl? I love the forbidden fruit."

In retrospect, I should've just left it right there—that would've been the mature thing to do. But in the end I couldn't leave it. I've thought about why that was for some time, and partly it's because I think I'm a fourteen-year-old boy mentally, and I wanted to mess with him. Partly, though, it was also because this guy was my gender and he was out there ruining our reputation. He was a scumbag, and I wanted to punish him.

So naturally, I flirt with him. I say, "What's it like to be so famous?" And "Watch Me on TV" reveals that the reason he has that screen name is that he appears once every couple months on some CNBC show at something like three in the morning. I couldn't believe this guy. He's trying to leverage that into sex with hot women, on the side?

I keep going. "Hey, you're so famous," I write, "and I've always heard famous people can do some pretty crazy stuff. What's the craziest thing you've ever done?" He says, "I'm so crazy, I'm going to run for political office." Great, I think. This is what we need: more politicians who pick up women on the internet. Then he tells me that he has "some pretty wild fantasies."

"Do tell!" I say. I was starting to break a sweat.

"I don't know," he demurs, "they're a little risqué." I tell him not to worry. "I can take it. You can say anything to me." It was a total setup.

He emails me this two-page letter, a detailed description of how Michelle is wearing this fur coat in a strip bar, and she's got on a black bra and her nipples are hard. She's grinding her crotch into guys' faces. And it goes on and on, only getting more graphic. When I get this, I am, as you can imagine, very excited.

So I emailed him back. I decided to take a different tactic now. I wrote, "You disgust me! You want to treat me like trash. I can't believe you would consider me a piece of meat who would grind my crotch into guys!" Suddenly, he is all groveling and apologetic, saying, "Oh, I'm so sorry, I didn't know." That was when I decided I'd done my best to teach the guy a lesson, and it's time to move on. I wasn't Chris Hansen from To Catch a Predator. That guy gets to sit there all day doing this, but me, I've got to find Michelle a boyfriend.

She agreed to go out again with the guy with long hair, the music teacher. They meet for dinner. When she comes home afterward, I'm eager to discuss it all. "So, how was it?" I ask. "He's nice." She shrugged. I knew that was the death knell.

Although it broke my heart, she did not go on a third date with this guy. I did set her up with a bunch of other guys. It turned out that she didn't end up with any of them, but she did end up with an old friend of hers that she knew from a decade ago. So even though I can't take full credit, I do like to take a tiny bit of credit. The way I rationalize it is that Michelle hadn't dated in five years before I put us on match.com, so in a sense, I got her back into the dating mind-set. Yes, it was probably delusional, but I didn't care—I felt good about that.

And for me, the online dating was one of the greatest experiences of my life. I loved it because I got all this positive feedback I wasn't used to, and I also loved how I got to see this side of men that other men typically don't. I got to see the sleazy guys that I kind of expected, as well as the guys I didn't expect—men who were very emotionally vulnerable and open and romantic.

Thinking about those men, I decided I'd do one more thing as Michelle. I searched the website for "lonely and depressed" and saw this guy with a profile that said, "I live at home with my sick mother. I take care of her. I have no life. I'm a loser. I go to work. I come home. I play video games. And I'm really depressed." I wrote to him as Michelle and said, "Listen, we can't date because you're in another state, but I just want you to know that I think it's wonderful that you take care of your mother. I think you're a rock star, and you're gonna meet some beautiful woman someday soon, and you're gonna make her very happy."

I felt that was important to do, because with great beauty comes great responsibility.

Taking the RISK!

A Q&A with A. J. Jacobs

You're used to writing for the page, but this story was originally spoken conversationally on the stage. How does that make you feel?

I try to make my writing as conversational as possible, so I think it's a good fit for me.

Are there any parts of the story that you feel need tweaking now? Why?

I wish I could redo the whole experiment now. In the age of Tinder, it might even be crazier.

Michele Carlo

The Gift

It was just a typical Tuesday a couple of weeks before Christmas. I came home from school and, as usual, went right into my bedroom, where instead of starting my homework, I opened up the window and went out on the fire escape, where I lit a cigarette, took out my mini boom box, and tried to get my favorite radio station's signal so I could finish a mixtape. That station's signal was weak in my part of the Bronx, so I had to wrap the boom box antenna in tin foil and point it toward the Whitestone Bridge.

In between making the tape and smoking the cigarette, it started to snow. So now I was trying to keep the snow off the boom box, too, so I didn't hear my mom at first when she came into the room and said she needed me to stop what I was doing and run to the store for her right now. And I thought, "Aw, man!" That was the last thing I wanted to do! When she told me what she wanted me to get for her, it was the last thing I wanted to get…Kotex. And not just any box of Kotex, but the "Super"-size box, which was big and purple with bright yellow letters. A box so tall it stuck out of any bag it was put in, so when you were carrying it down the street, anyone who looked at the bag (and you) knew you were the one that was bleeding…a lot. And when you're fifteen, you really don't want someone looking at you and knowing you are bleeding.

I growled to myself and stomped the five blocks to the drugstore, swearing that if I ever had a daughter, I'd never make her go out and buy my menstrual supplies. At the drugstore, the pimple-faced, four-eyed cashier gave me that weird, knowing look as he rang up the box. I stomped out of the store and started to walk home, when all of a sudden, I felt a gust of wind as two boys whizzed past me, grabbing the bag out of my hand as they slid down the block.

Genre:

Brit + Co, "12 Books You'll Want to Read on the Beach This Summer"
Amazon, Best Books of the Month
AOL.com, "14 Beach Reads"
Kobo, Most Anticipated Nonfiction, Best Books of the Month
"RISK! will move you to live fiercely and share your wildest truths!"
—John Hodgman, actor, humorist, and New York Times bestselling author of Vacationland
"[A] fascinating book...Naughty, funny, and scary in ways that will make you think, feel, and maybe even want to share a story that you never thought you'd dare to."—MetroSource
"Electric, daring, bold, ribald, terrifying. And that's just the first five stories."
—Dan Kennedy, host of The Moth storytelling podcast
"RISK! gives a platform to stories rarely heard, to people rarely represented and their most insane experiences. This book pushes us to live lives that inspire stories like these, to take risks you wanna live through to tell the stories about."—Ilana Glazer, co-creator and co-star of Broad City
"Powerful...The writers in RISK! are unafraid to bare their souls. These stories prove that when you take a chance--in storytelling and in life--anything can happen."—Lisa Lampanelli, Comedian and playwright
"From out-there tales of cannabalism and almost murder (yes, really) to provocative stories of identity and gender, this collection will make you gasp out loud and perhaps inspire you to live a little larger."—Mind Body Green, "The 5 Books You Won't Be Able to Put Down This July"
"If you love hearing about real life stories that range from embarrassing to heartwarming to sometimes shocking, you're going to love RISK!"—Brit + Co
"RISK! uncovers life at its most hilarious and terrifying. Each story leads readers over a tripwire and leaves you thinking, 'Wow...'"
—Glynn Washington, host of WNYC's Snap Judgment
"Evoke[s] both laughter and sadness...These fascinating, affecting confessionals are sure to reach readers beyond the podcast's scope."—Publishers Weekly

On Sale: Jul 17, 2018
Page Count: 400 pages
Publisher: Hachette Books
ISBN-13: 9780316478281