Illustration by Roberto La Forgia

A Sri Lankan monk once told me, “There is no doubt: if you follow the five precepts, you will be happy. You will live a good life.” We were standing outside the Mahabodhi Temple, in Bodh Gaya, India, discussing the Buddhist path for lay followers. At that point in my life, the monk’s words struck me as uncomplicatedly true. I was living in a Buddhist monastery as part of the Antioch Buddhist Studies program and observing the five precepts with such fervency that I wouldn’t borrow my roommate’s flashlight for even a minute without asking first. “What if she comes back to her room and needs her flashlight while you have it?” my teacher asked sensibly. “It’s a way of avoiding unnecessary complications.” The four months I spent in India were undoubtedly the happiest, simplest days of my life.

So I have complete faith that Shakyamuni Buddha knew what he was talking about when he offered a group of five hundred lay followers a prescription for leading a virtuous life, as told in the Dhammika Sutta: do not injure others, lie, steal, consume intoxicants, or “go with another man’s wife” (nowadays understood to mean “engage in sexual misconduct”). But these guidelines are much stickier to apply in the “real world” than in an Indian monastery filled with devout meditators and robed men and women. Back in the States and back into the swing of college life, I once again began to lie for the sake of convenience, get drunk a couple of nights a week, sleep with people I didn’t love, and subject the ants in my kitchen to death by tile cleaner.

Apparently I am not the only American who considers myself a Buddhist even as I routinely break the precepts. Chögyam Trungpa Rinpoche, the founder of the Shambhala lineage, famously showed up drunk to dharma talks and was known to have had sexual relationships with students. And Richard Baker Roshi, Shunryu Suzuki Roshi’s successor as abbot of San Francisco Zen Center, was pushed out of the organization following an affair with a married student, which catalyzed long-simmering resentments about his leadership style. In a 1985 Yoga Journal article, Jack Kornfield wrote that of 54 teachers and gurus he interviewed, 34 said they had been sexually involved with their students.

It’s no coincidence that the most controversial transgressions against the precepts in fledgling American dharma centers have been related to the open-ended admonition against sexual misconduct. The difference between a white lie and a manipulative untruth is relatively clear; sorting out the wholesome signals one’s body gives from the unwholesome ones presents a much more complicated challenge. It actually took me several years to realize that simply feeling attracted to someone is not a good enough reason to sleep with him.

I’m not sure where I got the idea, which I carried with me throughout college, that pleasurable sex was a virtuous, guilt-free activity. This outlook was at least partly societal: the general consensus among my peers was that orgasms made you happy, pure and simple. And they did make me happy, but they also irrevocably tied my life, however trivially, to the person who gave them to me. Sexual contact is always a commitment, if not to a relationship, then to future dealings—a talk, awkwardness, avoidance, an unrequited crush—stuff my Bodh Gaya teacher would call “unnecessary complications.” As an undergrad, I failed to accept this. I noticed the anxiety caused by sexual encounters, but I never considered changing my behavior. I suppose I had an idea that being open with my sexuality indicated that I was liberated, a freethinker who acted as she chose—and the baggage that came with that freedom? It was just something I had to learn to deal with.

Perhaps this is not so different from the thinking that gave rise to infidelity and teacher-student romances in emergent American sanghas of decades past. Just how hard and fast does the precept against sexual indiscretion need to be? Turning to the Dhammapada for guidance, we are presented with a seemingly unequivocal view: “Whoever [breaks the five precepts],” the Buddha is quoted as saying, “digs up the roots of himself even here in this very world.” But Shakyamuni’s overarching message throughout his life was that one must be one’s own wisdom. In the Kalama Sutta, he states, “Do not go upon…what is in a scripture. Kalamas, when you yourselves know: ‘These things are bad’…abandon them.” I read this as: always follow the five precepts. And figure out what that means on your own.

Indeed, since the publication of Kornfield’s article 20 years ago, dharma centers throughout the US have struggled to settle on appropriate interpretations of the precepts. Some centers have adopted a strict policy of disallowing sexual relationships between students and teachers. The San Francisco Zen Center leaves the option on the table, but only after a period of long and careful consideration. And Shambhala firmly discourages sexual relationships between teachers and students, but stops short of instituting strict rules.

Just as Buddhism in America underwent, and continues to undergo, a process of evolution, Buddhists are challenged to take a similar journey on a personal level. In a culture where one-night stands and “friends with benefits” are accepted as integral to the young adult experience, it took me years to develop a healthy relationship to sex that was wholly my own. Throughout college—notwithstanding my semester in Bodh Gaya—I created undue strain for myself and others by entering sexual relationships casually, often when my thinking was clouded by drinking. If I was having so much fun, I couldn’t be doing anything wrong, right? Twice, I woke up next to someone I couldn’t even bring myself to kiss in the sober light of morning. And these were guys I really liked—as friends. I had to endure weeks of awkwardness before our friendship returned to normal.

For a while, I experienced the closest thing to religious guilt that I’d ever known. Why couldn’t I have simply followed the precepts in the first place? I had always had faith in them; I just hadn’t translated that faith into action. Once I started paying attention to the sense of regret I felt after these experiences, though, I began to develop a “real-world” commitment to the commonsense wisdom of the precepts. Thanks in part to the Buddhist conception of regret as an opportunity not for self-flagellation but for change, I soon saw that I simply needed stricter standards for my conduct in order to make sure I handled my romantic life responsibly and with respect.

In At Home in Muddy Water: The Zen of Living with Everyday Chaos, the Zen teacher Ezra Bayda writes, “The difference between experiencing our sexuality as heaven or hell is rooted in one thing only, and this is the clarity of our awareness.” For me, living up to self-made standards requires not harsh policing, but clarity. (Never drinking hard liquor or removing any of my body hair before I go out helps, too.) If I’m considering getting intimately involved with someone, remembering the regret that I’ve felt in the past is usually enough of a motivation to act mindfully. I ask myself questions like “Would I want to kiss this person if we weren’t drinking Coronas and dancing to the Pet Shop Boys?” or “Do I really think I can look past this guy’s homophobia just because he has his hand on my leg in a parked car?” In the aftermath of my most recent heartbreak, which put an end to a two-year emotional roller coaster, I realized that all of my (extremely flawed) relationships so far had been driven by sex. With this revelation came a sudden sense of calm, the ticker tape of my self-censuring thoughts snipped mid-spin. “Oh, that’s what’s causing this pain,” I thought. “This is behavior I can change.”

I might have spared myself some heartache if I had taken at face value the Buddha’s warning in the Vipaka Sutta that breaking the precepts “leads to hell.” But I needed to have an experiential understanding of what sexual misconduct—and hell—meant for me. Without this, the precept would be a meaningless command that I would have little incentive to obey.

This doesn’t mean that my struggles with the precepts are over. Just the other day, I made out with someone I don’t much care for, caught up in the moment. Even though I had no interest in dating this guy, I found myself hoping he’d call me later. Fortunately, he didn’t—so I got to simply notice the unnecessary emotional energy the encounter had used up, and remind myself to continue trying to be more careful.

At a 1993 symposium with twenty-two Western Buddhist teachers, the Dalai Lama remarked that in a few rare cases it is acceptable for gurus to use sex to help their disciples achieve awakening—but the example he cited was of an ancient lama who was so highly realized he could also fly. Moreover, many people report that Trungpa Rinpoche often delivered crystal-clear dharma talks while intoxicated. Which is not to say that his drinking was unproblematic—just that all of us have different limits, and that we must each grapple with our own. The wonderful challenge of Buddhism is that it does not offer any absolute formulas for virtuousness. In the Silabatta Sutta, the Buddha asks Ananda if every precept and practice taught by the dharma is holy. Ananda replies, “Lord, that is not to be answered with a categorical answer.”

This article was originally published as a Tricycle Web Exclusive in 2008.