Cheating from a Multitude of Perspectives

A long read from a Sexologist

Leanna Wolfe, PhD
The Scarlett Letter
17 min readNov 15, 2020

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Sexual Cheating is deeply embedded in the human condition. Considering that humans are by nature a non-monogamous species who readily become fascinated with new (dopamine-generating) opportunities, cultures everywhere grapple with it. Followers of every version of the Jewish and Christian bibles have been admonished to:

“Not covet they neighbor’s wife (or house or ox)”

And more explicitly in the seventh commandment,

“Not commit adultery.”

In biblical times adultery was more narrowly defined than it is today. Biblical patriarchs were allowed to have multiple wives and concubines and were free to have sex with consenting single women. They were forbidden, however, from erotically engaging women who were married to other men. These concerns were largely about property rights; a married woman (as well as a neighbor’s house and ox) were private property and were not to be unwittingly occupied, used or sexed by anyone but their rightful owner.

My father was the first person to tell me about cheating. His telling was in the form of a story of his friend Harry who maintained a long-standing absolutely-hidden affair during the course of his life-long marriage. One evening at the opera, he saw Harry in tow with the other woman; the two men exchanged an acknowledging wink, and no introductions were made. My father’s telling of the story did not even wince of the emotional thunderstorms and strategic challenges that contemporary cheating can imbue. Ultimately, Harry’s wife never found out and Harry passed away as a respected, loving husband and father.

I don’t believe my father ever cheated on my mother. His reasons were tied to his marrying at the seasoned age of 45. As it was related to me, he’d had many years to “sow wild oats,” and thus had not suffered from an abyss of sexual variety. As for my mother, her first lover was a married man who initially lied to her about his already-taken status. She respected the rules of the day regarding the comportment of secret lovers and enjoyed the sweetness of the connection until she eventually met my father who was fully available for marriage.

The first time I dabbled in the world of being a secret lover was when I met Guillermo, a National Geographic photographer in Mexico. I was so focused on being mentored in my anthropological studies that it barely dawned on me that Guillermo was married. While I was frustrated by Guillermo’s unwillingness to be in touch, retaining the integrity of his marriage was no doubt more important to him, than assisting me with my professional aspirations.

While my college boyfriend Terry and I had an open relationship, our dalliances with other lovers rarely ignited the intense emotions associated with contemporary adultery. Six months after we met I took a four-month solo-trip through Western Europe. Being curious, cute and 20, I had many invitations and a couple of sexual adventures. One was with a Dane I’d met on a train in Copenhagen. He invited me to share his home (and his bed) during my visit. Following the visit my period disappeared, but sensing no other bodily changes, I rightly assessed that he had not gotten me pregnant. Back home, Terry was using my wall calendar to mark off his various dates with a girl named Janel. Upon my return, Janel was downplayed and Terry made me feel like I was his “one” until I’d had too many cups of morning coffee with his roommate Rick. After a couple of weeks of whirlwind romancing, Rick migrated to becoming a casual-lover and lifelong friend. I kept the calendar that recorded each of Terry’s dates with Janel, assessing that our break up had more to do with our mutual desires to engage the mid-seventies Sexual Revolution than any of our hardly-threatening dalliances.

My next opportunity to wince being cheating on was when Sean and I became partners in New York City in the late seventies. He’d just unfurled himself from living with a top-notch public interest attorney to move in with me a wide-eyed anthropology graduate student. Considering the stultifying possessiveness he’d weathered trying to do monogamy in the midst of the Sexual Revolution, we endeavored to have an open relationship. One night he returned very late (there were not yet cell phones for sending one’s GPS whereabouts) and explained that in the course of selling poetry on the streets of Manhattan, he’d met a cool couple and joined them back at their flat. While he failed to disclose any details of what had transpired, I felt jealous that I had missed out on what I imagined was an amazing encounter.

In our Manhattan world of the early eighties, all of the permissive rules of engagement that living-together-couples allowed each other were swiftly supplanted with strict monogamy once there was marriage and babies. Thus the darkness of contemporary cheating reared its head. The first emotional thunderstorm I listened in on was that of Gary and Anna, a young professor and his expectant wife. During Anna’s pregnancy Gary took up with Kim, a pretty teaching assistant, and then soon after his new baby was born, he pronounced his love for Kim and Anna filed for divorce. To me, Gary sounded like the extreme of cads; the whole incident heightened my wariness of marital expectations. I doubted that I’d ever be able to ferret out a true lad amongst all the cads in 1980s New York City.

Every time I’d soak in the jacuzzi following a workout at my Greenwich Village health club, another married man (often with a pregnant wife), would proposition me. In deference to my stirred up emotions over Gary and Anna, I’d flatly refuse. Then some ten years later, exhausted by my efforts to meet and marry “the one” I took refuge in becoming a secret lover. Every time I’d walk into a party, I’d find myself gravitating to the married men. I enjoyed the rush I’d feel when they’d remark,

“You are smarter, prettier and so much more fun than my wife!”

Being single I had little to lose (other than my time).

Ultimately, I had affairs with three married men. One, Ben, ensured that the whole affair remain a secret, generating an identity for me as a “family friend.” There were moments where I felt very tempted to tell his wife, but then I faced I didn’t really want him as a full-time partner and moreover had absolutely no interest in disrupting or destroying his marriage.

The second, Brad, was much more of a risk-taker and did little to cover his tracks. Soon into our affair (which was much more about love than sex), a righteous woman in our community informed his wife. All exposed, I was one of several women he was courting. While the others quickly disengaged, I took it upon myself to attempt to negotiate a compromise wherein he and his wife Sofia would open up their relationship for me to become a polyamorous second wife or a live-in concubine. Brad’s wife flat out refused and several years later when they eventually did divorce, she blamed me. My feelings were hurt in that all I had requested was that we all become “family.”

My third married man was Chuck who during the several years we navigated our polyamorous love affair made me feel exquisitely matched and very loved. While our home partners knew when we would be seeing each other, we generated many never-to-be-disclosed secrets. While orthodox polyamorists advocate full disclosure; the world we created together was tender. Our home partners could not fathom practicing compersion, the polyamorous term for having loving empathy regarding pleasure accessed with other lovers.

Perhaps the bliss Chuck and I accessed with each other was too potent. As much as she could, his wife invited me to become a personal and family friend. There were moments in which it worked, but mostly their home was filled with landmines waiting for me to stumble on and be blamed for the precariousness of their connection.

While my step-daughter was well-aware that my relationship with her Dad was polyamorous, Chuck’s children sort of didn’t know. They’d already weathered an attempt by a single woman to spirit their Dad away and the family had buckled in tight to assure them their Dad would never again leave. Back home, my partner, Jon, relished making fun of Chuck and telling me I looked way too smitten every time I’d return from a date or visit. In the end when the passionate cling between Chuck and I subsided; I did feel a sigh of relief. The tension was too thick all around.

Being a secret lover, who has little interest in destroying a lover’s marriage, is emotionally calm relative to the two other positions in the cheating triangle: cheating and being cheated upon. Having a penchant for disclosure and despising living a socially and emotionally partitioned life, I’ve only cheated once and that “once” was in the context of polyamory. I was dating a guy named Michel who had a best friend who was also named Michel. Several months into dating Michel#1 he announced that his best friend Michel#2 was immigrating to Los Angeles (they’d both grown up in Montreal). When I asked if they had ever shared a woman, he told me they had done it many times and that he would be happy to introduce me to Michel #2. As it turned out I really liked Michel#2 and happily dated them both together as well as, separately. I was in such bliss I could barely contain my pleasure when we’d go to parties as a threesome, rent hotel rooms altogether (leaving the maître di to giggle in wonderment) and have the most fun I could ever imagine.

At the time I was living with Jon who only knew I was dating Michel#1. I began to feel guilty that I’d told him so little. We’d endeavored to be honest with each other and I’d been harboring a big secret. The day I told Jon about Michel#2, he had a meltdown, especially hearing that I’d invited both of them over to share our bed while he was off with his lover Violet. The thought of me making love with two hot guys in our bedroom so boiled his blood that he tried to strangle me. I wrenched myself free and sought safe harbor at a friend’s house. After a couple of days, Jon calmed down and I promised I’d never again host a threesome in our bedroom. Soon after, I migrated into just dating Michel#2. That lasted for a short while, but Jon’s volatility ultimately scared them both away.

Being cheated on, the third position of the cheating triangle is no doubt a painful one. In that I’d tended to keep my partners on long leashes with quick-release collars, I’d largely averted any desire on their part to cheat. I detest possessiveness and consider flirting, light kissing and playful teasing to all be acceptable behaviors. To my knowledge, I’ve been cheated on just once. Many of my friends witnessed Jon’s interest in Violet. But none of them told me. Jon contended that (at least initially) he thought it would be a brief dalliance and that he would “handle it” (e.g. break it off with her). After several months of him coming home smelling like her cologne, guarding my access to his email (initially we knew each other’s passwords) and suffering “cartastrophes” like having his car battery die and not being able to get home until 4 AM, she decided to tell me.

Hearing what I might have suspected ended the sanctity of my relationship with Jon. Many times I wished she’d never told me; that he had privately “handled it.” Being witness to the intensity of their private connection was very difficult. The two of them were steeped in the dopamine of new relationship passion, while Jon and I, at best, accessed the oxytocin-rich attachment phase of long-time trusting partners. With the trust broken, the oxytocin in my brain crashed and all I could do was to scream and shiver. Not wanting to be the loser, I did what I could to persuade them to include me and become a polyamorous triad. It worked and then it didn’t.

Beginning in the spring of 2008 I shifted gears from doing informal “experiential” research on cheating to conducting Internet Surveys to collect quantitative data. Having a track record for doing survey research on polyamory and swinging, Dr. Ava Cadell invited me to be the Director of Research for her online enterprise, Loveology University. She was a mix of formal and friendly….and a delight to work with. I designed a quick 12-question survey which we linked to each of our websites. Respondents slowly trickled in;11 months later we had 1055 surveys with a 98% completion rate. Over the previous six years I’d conducted several surveys on the behaviors of people who practice polyamory and was accustomed to my surveys being networked by enthusiastic respondents. During a short survey window of two and a half weeks in March of 2008, 716 polyamorous respondents took my 50-question multiple partner survey with a whopping 99.6% completion rate.

Those responding to the Loveology University cheating survey were a completely different cohort. They were not an enthusiastic data-hungry community like the polyamorists; they were disparate individuals who enjoy accessing sexual topics on the Internet. Being that it was called a “cheating survey,” about 60% of the respondents had participated in one or more corners of the cheating triangle. They were hardly representative of the distribution of cheaters in contemporary America; a recent national survey clocked just 28% of men and 18% of women. My respondents clearly had an interest in and involvement with cheating with 67% of the males in committed relationships reported having cheated and 62% of the females reported having been cheated on.

I created the category, “Combo Cheaters” to describe the 72% of my cheating respondents who also knew they’d been cheated on. I noted that males in this category had the highest appetite for more, better and different kinds of sex as a cheating motivator. These males robustly justified cheating with nearly two-thirds citing a sexless marriage and almost half contending that their wives’ medical problems prevented them from having the kinds of sex they enjoy. Meanwhile, over half of the combo cheating females reported that there was “no justification” for their own cheating.

Age and gender figured strongly in participation in and assessment of the value of cheating. Of the females who had been cheated on, two-thirds claimed activities like cybersex, sharing emotional intimacy, light kissing, phone sex and cuddling were absolutely “cheating.” Finally, my research concluded that females largely cheat for “attention” while males cheat for “excitement” and to “live out their sexual fantasies.” Males consider cheating to be harmless if they are able to get away with it while females, even if they have cheated, still regard it as an immoral activity.

The following year Avid Media, the parent company of Ashley Madison, a notorious website that enables married people to connect with other married people for discrete encounters, contacted me. They were impressed by the work I had done on the cheating study and wondered if I would like to partner with them for a new study. My mouth watered thinking of the easy access I might have to a large data base of active cheaters and I readily gulped,

“Yes, it would be pleasure!”

Avid Media which is based in Toronto immediately began to draft numerous legal documents wherein rights were assigned, duties were explained and payments were promised. Due to frequent staffing changes, other than (now former) CEO Noel Biderman, the rest of the company was forever in transition. I was told that the company wanted to study the relationship between anal sex and cheating. They’d noticed that many of their members were checking off anal play on their profiles and wanted to investigate whether couples who were getting enough of this at home would be less inclined to cheat. My inclination as a Sexologist, was that the absence of anal play in the home erotic repertoire was probably not a big factor in whether a heterosexual couple would seek to cheat. While their observation was right that a growing number of heterosexuals were experimenting with anal activities, altogether this stuff was more of an add-on rather than a must-have.

Nonetheless, I kept my lips zipped-tight, quickly educated myself on the requisite paraphernalia by attending anal sex educator Tristan Taormino’s workshop at The Pleasure Chest, an adult entertainment store in West Hollywood. Brimming with information on butt plugs and Strap-Ons, I drafted a survey. To make the survey innocuous enough to attract many respondents (to fulfill the quotas laid out in my contract), I called it, “The Sex and Relationship Happiness Survey.” To not immediately offend the non-anally inclined, I began with basic demographic questions, queried about the respondents’ involvement in cheating and posed a series of questions about oral sex. Then I created toggles so that respondents who had no connection to anal activities would be quickly steered away.

The survey was approved and at the end of March 2011 it was launched through a link on the Ashley Madison site. Over a nine-week-period nearly 5,000 Ashley Madison members completed the survey. I was astounded. To generate perspective on the Ashley Madison cohort, I also sought participation from people on polyamory lists, people more specifically involved with anal play via Tristan Taormino’s network and Fetlife, a social networking site for kink aficionados. Altogether we attracted close to 7,000 respondents. I was in survey-researcher-heaven.

As I began to crunch the data, my suspicions about anal play not being a big factor in why people seek to have affairs were readily confirmed. While I ultimately did present, “Anal Play: Who is Doing it and Why?” to the Spring 2012 meeting of the Society for the Scientific Study of Sexuality in Los Angeles, Noel Biderman actually wanted a report that would “normalize cheating” in America.

We poured through the data and found what he referred to as a “smoking-gun” regarding oral sex patterns and preferences of the Ashley cohort men. Sixty percent of these men and a nearly half of the control group men believed that “other couples were having more oral sex with their home partners than they were.” The women in both groups were evenly distributed amongst the three choices “more,” “about the same” and “less.”

To me, these findings implied something about the significance for men regarding the act of receiving oral pleasure. While women tend to regard oral sex as a preamble/foreplay for intercourse, the visual and psycho-emotional sensation for men is significant. The act of having a beloved place his very private part in her mouth is both humbling and exquisite.

Our “most-smoking-gun” finding then appeared when we evaluated strategies for dealing with a home partner who refuses to provide oral sex. While two-thirds of our respondents reported that they’d “let it go and focus on what their partner likes,” more than a third of the Ashley male cohort claimed they would “have a secret affair” while less than eight percent stated they would “seek the services of a prostitute.” This interested me.

While my control group males were more likely to seek an open polyamorous lover than a secret lover, they, too, registered low (less than six percent) for seeking the services of a prostitute. This group of largely heterosexual, middle-class, married American men in their 40s and 50s, seek (if at all possible)to receive oral pleasuring from women who love them. Unlike other ethnic and class cohorts such as Orthodox Jews and working class Hispanics who routinely frequent prostitutes for oral pleasuring, these men see it differently.

I presented my findings at the November 2011 meeting of the Society for the Scientific Study of Human Sexuality in Houston, Texas and then in December 2011 my paper was published in the Electronic Journal of Human Sexuality. Avid Media had plans to do a press campaign, but their new public relations department was looking for something more sensational. In perusing my findings, they noted that nearly two-thirds of the women on the Ashley Madison site were actively cheating on their spouses and sought to sensationalize this in tandem with the oral sex data. To me, these two findings were unrelated.

Women who post profiles on the site tend to have cheating experience and seek more of the same. The men on the site differed little from my control group men regarding cheating experience; regarding marital happiness, they registered far happier than the women on the site. From what I could surmise many men sign onto the site to “check out” what is possible in case they might want to have an affair. When I isolated out the active cheaters from all of the non-cheating visitors, the Ashley women (as I suspected) were not driven to cheat for oral sex. Refusing to be part of a public relations campaign that skewed my well-analyzed data, I allowed my relationship with Avid Media to fade and was not paid the balance on the contract I’d signed with them.

I began to play with the data set and saw several fascinating contrasts between the views and practices of Cheaters and Polyamorous people. From 2012 to 2014 I offered these findings to nearly a dozen conferences around the country in my presentation, “Are Polyamory and Cheating All that Different?” Here I noted how Polyamorous people (relative to Cheaters) are more likely to be bisexual, be happy in their home relationships, and engage in more frequent sex with their home partners and more alternative sexual practices like BDSM and anal play. As for where they’d go for the oral sex they’re not having at home, as expected the poly people would seek it with their poly lovers and the cheaters would seek it with their secret lovers.

In my work as a sexological statistician, I was not party to the air-tight strategies cheaters use to keep their marriages safe. For this data, I’m indebted to several men who I’ve managed to cajole into sharing their stories. One was a man who sat next to me on a flight between New York and Los Angeles. When I mentioned I do sexological research on people with multiple partners, he agreed to “tell all” as long as I agreed to never be in touch with him again. Being that he chose to remain anonymous, I have not even given him a pseudonym.

During the course of our six-hour flight, he described how he hid his long-time lover from his unsuspecting wife. He used disposable cell phones and calling cards for making dates with his lover, assuring that there would be neither digital nor paper evidence. When he bought gifts for his lover he would always buy an identical gift for his wife so that no unexplained purchases would appear on his credit cards.

His dates with the lover were always paid in cash; one morning following a lovely night together, he took her out for breakfast. He was out of cash and had to put the meal on a credit card. To cover himself, he took his wife out to eat at the same place that evening and quietly paid cash for that meal so that she’d never suspect a thing.

When we discussed the details of sexual performance, he revealed that while he uses Viagra with his wife, he never needs a pharmaceutical boost with his lover. Did he ever have thoughts of leaving his wife for his lover?

“Absolutely not! She is emotionally unstable — marrying her would ultimately be a disaster!”

I met Moshe, a Jewish Iranian teacher at a local café. He’d responded to one of my personals ads, neglecting to mention that he was married. It took over an hour of chatting about this and that before he revealed his already taken status. Despite that he considers his wife cruel and combative, ending their long-standing marriage would be culturally inappropriate. He’d be exiled from his ethnic community and his wife and children would regard him as a pariah. For him, the only acceptable thing to do was to find women available for trysting with him in the late afternoons and to “golf” with him on Saturday mornings. As I listened to the tight boundaries he imposed on his consorts, I gained an appreciation for the energy cheaters expend to keep their secrets.

My final cheating enigma came in the form of Lawrence, a respected artist who lives in my community. We’d met at a party and soon started dating. As we grew closer he began to tell me about his lover of 20 years who lives several hours away and is married to a much older man. I asked if he and I became lovers,

“Would you then be cheating on her and would I then become a secret lover?”

We laughed about how my terminologies made this all sound so complicated. Ultimately, there were no conditions under which he would either leave her or tell her about me. As I released Lawrence, I assured myself that I had absolutely gone full circle in my exploration of cheating!

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Leanna Wolfe, PhD
The Scarlett Letter

I am a 67-year-old Sexual Anthropologist, Writer and Storyteller living in Los Angeles. For more about me see: www.wisewomansexandrelationshipconsulting.com