What I Regret Most about My Hyper-Sexual Past

“The Buddha once said, pointing out the obvious (as religious sages so often do), that all meeting ends in parting. If you can accept the truth of this and digest it, you will begin to realize that all your relationships are precious, for each one has taught you something unique that you could not have learned in any other way. Each of our relationships ought to be handled like a delicate gem, with full respect for its particular beauty.”

— Norman Fischer, Taking Our Places: The Buddhist Path to Truly Growing Up

The List

At some point in my twenties, I resolved to sleep with at least ten people and began keeping count. Later, upon reaching that milestone, I upped it to twenty.

Worth noting: I didn’t have sexual intercourse until grad school. First, because my high school love determined that God was only okay with oral sex out of wedlock (nothing else). Second, because when I tried with my next boyfriend, it didn’t work.

Only after my grad school boyfriend came along was intercourse normalized and effortless. Prior to that, a growing fear that I’d never have sex led me to set ten, then twenty partners as an acceptable quota.

Surely by then I’d be normal.

In any case, part of tallying lovers I never really wanted goes back to sense of self (or lack thereof). I wanted to feel interesting, edgy, sexy, desirable, and, most of all, enough. If I hadn’t had sex in a while, it seemed necessary to prove I wasn’t just the quiet, nerdy one.

I didn’t add oral to the initial tally, adhering to my high school boyfriend’s decree of What Counts. Once I started dating women, however, everything got confused. Was oral with women equivalent to intercourse with men? Did sexual relations but not intercourse with men also make the list? What was legit and fair?

I eventually decided to track everything (only in my head, thank god) but still kept intercourse separate. Somehow, this hetero-glorified, cis-male-centric act held more clout. Somehow, it made me more worthy.

Even when I didn’t enjoy it. Even when it was completely devoid of pleasure — never mind love and connection. Even when it left me physically, emotionally, and spiritually numb.

When The Number increased, I felt better about myself. Look at me, figuring this edgy, liberated, dark academia thing out. First with guys. Then as a lesbian. Then slapping on the more accurate sticker of queer bisexual flexible.

Keeping count

In this way, across the years and in between more serious relationships, I collected lovers — oftentimes one-night stands or thereabouts.

There was the time with my DC hair stylist Kim, who preferred drunken sex with porn streaming in the background. There was the time with a total stranger who kept his money belt on as we fucked in a cheap Bangkok hostel.

There was the much older man from AOL Messenger who wanted a plaything for himself and a companion for his young daughter. He took us to an amusement park and pretended we were both his kids. (I stopped seeing him thereafter.)

There was a time or three of sex with friends, each of us desperate to connect and fend off depression, despair, and hollowness after a night of partying.

There was my dear Norwegian friend Nils, whom I’ve known in perhaps the most homes of anyone. Our paths crossed first in Cairo, where we were studying Arabic; then in Washington, DC; then Chiang Mai, Thailand; then Lijiang, China. We had sex only once, in Thailand, and it was after a day of me sobbing over a (totally separate) love triangle fiasco.

Nils has lots and lots of sex (along with an honest-to-god foot fetish) and it was very good. Still, we both seemed fine to leave it there, and he was leaving the next morning. When we next met in China, our sharply divergent political views erupted in self-righteous, non-listening fury. We parted ways and swore the parting was forever.

That was not true, in the end — I’m ever eager to kiss and make up. Nils and I disagree on very big things, but we reconciled once our tempers cooled. He remains a treasured if faraway comrade.

Others on The List were less lasting. Raiff, for instance, picked me up while I was living in Takoma Park and newly heartbroken over another. He was immersed in yoga, enamoured with Bob Marley, and exceedingly chill.

Originally from Cameroon, Raiff grew up in Jamaica and gave off a caricatured Rasta vibe — all long dreads, red, green, black, and gold. We partnered during handstand practice and dated for a minute thereafter.

Similar to me, Raiff had an “eating thing.” He was Rastafarian vegan, yes, but also doled out food with an ascetic eye, courting spiritual awareness with weed and malnourishment. The both of us were already skin-and-bones; Raiff made sure it stayed that way.

Given my affinity for anorexia and yoga highs, I was all in with deprivation but not weed — a glitch that made fasting harder and impatience plentiful. Things took a long time. Plans were nebulous and largely theoretical.

Mostly though, I couldn’t take the snoring. Louder than any I’d ever known, it kept me up entire nights and ultimately led me to ghost him. My fury at his sleeping soundly — but definitely not silently — only to stretch contentedly at dawn and expect morning sex was too much. I added to the tally and moved on.

Doctor in training

In my thirties during Chinese Medicine school, any romantic relationships were short and not particularly passionate. I was immersed in studies and cared more for straight A’s than intimacy.

At the start of my first year, there was a fellow meditator at the Buddhist centre in town. Being with him was calming but lacked chemistry. I broke things off the minute exam stress made ordinary annoyances insufferable.

Later that year, there was a senior schoolmate. She was the opposite of calm — always feigning nonchalance while subversively courting chaos. While I found her ability to warp reality mesmerizing, I wasn’t into the perpetual lying that went with it. We didn’t last long, she edged towards stalker status, I blocked her from email and phone.

My second year, there was another girl — someone I met at Pride and who was wonderfully removed from the college scene. Being with her felt right and full of butterflies…until she veered into mother issues and therapizing on the third date.

While I’d have been a willing participant previously, now studies came first. I had no time, tolerance, or energy for it and ended things without conversation. Given her brand of co-dependency and indifference towards boundaries, the move felt like self-defence. Still, it lacked grace in execution.

My third year, I crushed on a classmate for a while. Despite being straight, she led me on unabashedly. Our increasingly physical flirtation-ship lasted about a month. I actually felt happy again.

It, along with said happy, came to an end when she wasn’t getting what she’d hoped — namely, an academic boost and inside access to one of my male mentors. In the space of a day, she replaced me with another bestie from our class. I felt hurt, foolish, and as though we were back in grade school.

My fourth year, there was a senior Chinese Medicine doctor — someone I respected greatly but was not into sexually. Amidst exam stress, I again ended things abruptly, without warmth or warning.

My fifth year, there was a punk friend with a mohawk, numerous piercings, and the most tender heart. Like me, he was bisexual, and his serious relationships before and after us were with men. I tried to pull closer and feel more than friendship, but it just wasn’t there.

These fourth and fifth year partners were too emotionally needy and “nice” for me back then. They adored rather than abuse me, and this, for me, fell flat.

I was thoughtless, self-absorbed, and emotionally hovering around age 16. Hooked on a fucked-up version of love and victim story, I victimized other hearts.

Sex for texts

Also on The List were cases of flat-out prostitution. A stranger who paid me hundreds for blow jobs in a fancy hotel. An ex who paid me for sex after I broke his heart.

I needed the money, yes (specifically, for textbooks). Also, I thought it was edgy and cool. After all, I was a non-coerced adult agreeing to a physically safe, clearly defined exchange — one in which I was fully sober but could dissociate quite masterfully.

I’d go inside, numb out, get paid, walk away. It wasn’t so different from certain other jobs I’d held (or certain relationships). Much easier, really.

In the end though, the actual experience was repugnant. This isn’t an ethical thing, and I have zero judgment if sex work works for you. For me, it did not.

Because of that, such instances were exceedingly few — a short “phase,” if you will. Mostly, I just added to the tally with cursory relationships and free-of-charge flings. I loved my freedom and living alone. I still love my freedom and living alone.

But now sex with someone I’m not into holds zero appeal, even if they were to pay in one currency or another. Prostitution, after all, takes many forms — most of them everyday, acceptable, expected exchanges.

I’m bored with that: Consciousness is bigger. Life is bigger. We are worth more.

The Other Woman

All that is true, and I don’t regret my managerie of sexual encounters. It was part of trying things out and trying on alternative expressions of self. It was part of learning that society’s dictates about what sex is and what counts don’t always apply. It was and is part of my story.

Any regret in this realm has to do with those I hurt along the way. This includes sleeping with people who were cheating on others. I can’t fathom doing that now — it’s enormously selfish, hurtful, and unethical.

As I review my past around it, I take full responsibility for all wrongdoing. I made mistakes. Those mistakes wounded others.

In my twenties, I knew I’d never cheat but rationalized that I wasn’t the one doing the cheating. If they were going to cheat on their partners anyway, might as well be with me!

I imagined myself a badass loner who was free and cool and rebelling against small town roots. I was proud of this version, which stood in sharp contrast to the bullied, interminably shy teacher’s pet who came before.

Also, to be fair, I usually didn’t know the person was cheating until after. One of my older step-cousins, for instance, sent me reams of poetry and led me to believe his marriage was over and thus open. In retrospect, I should’ve known he was lying long before receiving a vicious email from his wife tearing me to shreds. In retrospect, I was choosing not to see.

Another friend of a past love invited me to his gorgeous home and ceramics studio for the night but made sure I was unceremoniously deposited back at the train come morning. Only under the sheets did he mention a “girlfriend” who was out of town, dropping the news so casually I felt sophomoric making it a thing.

Then there was the tale of my professor and mentor Muhsin, who, with both my friend and me, was cheating on his wife.

I wasn’t fully aware of the “cheating” in these cases. Except that I was. I didn’t want to know and actively ignored the signs. I tuned out intuition because it was in the way.

Now 46, looking back at the twenty-something version who did this, I try to forgive her.

I also remember her when I see present-day twenty-somethings doing something similar. They’re on that chapter now; I was on it back then.

Feeling justified, we act from our wounds but make more in the process, growing a shared circle of hurt. My heart aches for all of us.

Final tally

The tally here doesn’t include anywhere close to everyone who made The List. I’ve skipped over quite a few and lost count along the way. Suffice to say, it exceeded ten, then twenty, then…I’m not sure.

I’ve blocked a lot of it out, really. It, on the whole, was not particularly pleasurable and was not the stuff of conscious growth and transformation.

Some people in the mix I barely recall. Most I barely knew.

Thinking of them now, I recognize that they, like me, hold whole worlds inside. The entire Universe even. We didn’t honour that in each other. I did not honour that in them.

This is a loss. This was based on the impossibly misguided, self-centred assumption that everyone else is at some normal baseline while my own life is unique in its painful vicissitudes.

That’s not good enough.

Now, when I look at you — as best I can and as consciously as I can — I see you. I honour you. Your heart, your body, your light, your soul.

Thank you for reading. I’m a doctor of Chinese Medicine and write about sobriety and soulful living. Find all my links here: