Sleeping with the Boss

Call it the Letterman Effect: Monique El-Faizy explores the darker side of having an affair with the guy in the corner office.

It's not unusual for an ambitious young attorney to curry favor with her law firm's higher-ups by fetching them coffee and plying them with office gossip over happy-hour cocktails. But when Lisa Scarso, a tall, coltish 29-year-old lawyer for a scrappy Bay Area public interest firm, invited her supervising attorney to lunch, she wasn't trying to get in good with the boss — she was trying to bed him. "He had these beautiful eyes" — one bluish-green, the other brown — "and that was kind of it for me," she recalls. Their flirt-filled lunch was soon followed by another, and while walking the long way back to the office, they ducked into a Laundromat, where Scarso hopped up on a dryer to make her case, eye to eye. Her boss was decidedly skittish. Though he was single and only five years older than Scarso, an office romance with an underling was considered taboo by the senior partners — never mind that it would obliterate his credibility with his other charges. Over dinner later that week — "I remember talking him into it," Scarso laughs — he relented, and the pair began to discreetly see each other. For fun, she'd slip into his office, sit on his lap, unbutton her shirt, and put his face between her breasts. All the while, she insists, her colleagues suspected nothing.

As attracted as she was to him, Scarso concedes that the subterfuge, coupled with the sheer ballsiness of their affair, was a major turn-on. "I never felt that there was a power disparity. If anything, I felt more powerful, if only because very often I was the initiator," says Scarso, who eventually left the firm for unrelated reasons. Only then did she make public her relationship with the attorney, whom she ultimately stayed with for five years before they amicably parted ways. Besides, she adds, for a young, attractive woman pulling 12-hour days in the office, the relationship was exceedingly practical. "People sleep with who they have access to. You become attracted to who you see on a daily basis."

True enough, sex in the workplace is rampant. According to a recent survey by, more than 40 percent of workers admit to dating someone at work over the course of their careers. Of those who romanced a colleague in the last year, 34 percent said it was with someone in a higher position at the company, typically their boss. (More often than not, it's women hooking up with a male supervisor — 47 percent versus just 38 percent of men.) The workplace has become a sexually charged arena, populated by neatly pressed cadres of driven men and women putting in long hours side by side, often under intense circumstances. They work together, eat together, and, of course, drink together, capping off a grueling day with a few highballs at the nearest watering hole. Is it any wonder this alchemy of ambition, angst, and alcohol produces so much sexual tension, whether it's on a Hollywood soundstage or in a mahogany-paneled executive boardroom? There's just something about working together on a big project one-on-one that forges intimacy. Watercooler liaisons are so common that they've spawned a lengthy and impressive list of power couples: Barack and Michelle Obama, Bill and Melinda Gates, Chelsea Handler and Comcast chief exec (and E! Entertainment overseer) Ted Harbert — they all fell in love on the job and, more importantly, one held a clear position of power over the other. (Full disclosure: I met my husband — who was my boss — while covering the collapse of the Soviet Union for a British TV network. He hit on me, I demurred, we ended up marrying and having two kids together.)

Yet despite the countless examples of illustrious couples who have made it work, shagging the boss remains for many employers a serious career taboo, on par with fudging a résumé or posting pics of your Girls Gone Wild Cabo vacation on Facebook — wildly inappropriate at best, a fireable offense at worst. Workplace romances are so fraught with potential problems that 12 percent of American companies have explicit policies regulating them, according to the American Management Association. That's largely to avoid exposure to sexual harassment lawsuits. But there are subtle, less calculable dangers a company courts when a manager gets involved with his subordinate: Nasty rumors begin to circulate; workers spend less time working and more time gossiping; morale invariably suffers.

Case in point: In the wake of the David Letterman scandal, former Late Night scribe Nell Scovell, writing for, conceded that while she'd never been the target of her boss's advances, Letterman's notorious on-the-clock hanky-panky nonetheless created a generally "hostile" work environment that favored some women over others. This in a workplace where female writers were as scarce as 9/11 punch lines. (Scovell, who wrote for Late Night in the early '80s, points out that in 27 years, Late Night and its successor, the Late Show, hired only seven female writers.) And one need only look at the eye-popping list of perks Letterman's latest paramour, Stephanie Birkitt, an assistant nearly 30 years his junior, reportedly scored to understand what kind of insidious favoritism Scovell is talking about: Birkitt earned an astonishing $200,000 a year, appeared on-air several times (even she looked embarrassed to be there), and reportedly enjoyed vacations with the Letterman clan. A tacit quid pro quo existed for women who had sex with high-level Late Show staffers. "Did that make me feel demeaned? Completely," says Scovell, who writes that sexual politics ultimately drove her to find another job. (She went on to write for Coach and Murphy Brown.)


man and woman making out between shelves of files

(Image credit: H. Weis)

Scovell's assessment of the Late Night milieu during her tenure there reveals another dirty little secret about office romances: They are rarely ever secret. When then-20-something British newspaper editor Danielle Janson was introduced to her boss, a married man with kids, the mutual attraction was palpable. "It was one of those things that just seemed inevitable," she recalls now, some 20 years later. The grinding deadlines and late nights fueled the relationship, which quickly became intimate. "I was just at the beginning of my career, and it was all so exciting," Janson says. Both went to great lengths to maintain discretion, always careful never to leave the office at the same time. Yet both were oblivious to the fact that their newsroom cronies were in on the secret — they intuited it — and routinely placed bets on how long it would take for the other to leave once one had packed up for the night. At the time, Janson says she didn't think the affair had any negative impact on her standing in the office. But years later, it still comes up in conversation with former colleagues. "Looking back, I suppose some people in the office took me less seriously because of it," she concedes.

At the time, Janson was in her 20s and five years younger than her lover. That's worth noting because, let's face it, it's usually the young ones who are especially receptive to the charms of a powerful boss and who often underestimate the professional and emotional fallout when these hush-hush romances go south. Jessica Wakeman, a 25-year-old Manhattan-based blogger, says that while she interned at a prominent magazine, she struck up a friendship with one of its editors. For over a year, she was his special project. He pored over her writing, spent precious time giving her detailed feedback. "When you're young, you don't know that many successful people in your field, so when someone older starts paying attention to you, it makes you feel special," Wakeman says. She knew he liked her, and she enjoyed the bragging rights. "It felt great to name-drop with my friends that I was hanging out with this editor at a big magazine." One night, after her internship had ended, he invited her over to watch movies. By the end of the night, they were in bed. Pretty soon, she was smitten and regularly sleeping at his place.

When she scored a full-time gig working in a different department at the magazine, Wakeman says she was ecstatic. But her mentor-turned-lover chafed at the idea. Usually warm and friendly, he barely acknowledged her presence during the day. When she confessed that she was in love with him, he promptly broke things off. Wakeman was devastated. "I thought I was adult enough to handle it, but all he saw in me was a younger woman who graduated from NYU a year earlier," she says. "If I was delusional about anything, it was that we were peers." Wakeman took a job at another publication a short time later.

Did her editor take advantage of Wakeman's naïveté? Perhaps, but officially it doesn't count as sexual harassment. Current law bans sex-for-favors and behavior that creates an "intimidating" workplace. (In other words, you can't promise your assistant a raise for a little boardroom nookie or plaster your cube walls with naked pictures of Robert Pattinson.) But the law is decidedly murky when it comes to likelier scenarios these days, like the fresh-out-of-college office naïf who welcomes the advances of an older, horny boss. Take 23-year-old Ava Smith, who began working at a small New York nonprofit shortly after graduation. At first, she was grateful for the attention lavished upon her by her boss. Though he was 20 years older, they clicked instantly. Smith wasn't troubled by his frequent invitations to grab beers after work, nor was she suspicious when he invited her out for the occasional dinner. It was on one of these outings that he confessed to being infatuated with her. "I guess I was flattered," she recalls. "But I was also really scared because I didn't know how to respond." Though she had reservations, she nonetheless went along with an affair. He was a big shot at work, smart and worldly, and he was interested in her.

But things quickly got weird. Soon, he was furtively grabbing her ass in the office. Sometimes he'd pull her into the back room and coax her into having sex with him. Then he began taking her to hotels in the middle of the day. She knew their relationship had become unhealthy — a distraction for her, a near-obsession for him — but says she didn't want to compromise her job by putting an end to things. "I just felt that I couldn't get out of it because he was my boss. He was like a puppeteer and I was the puppet, and he was just pulling the strings. I felt like I didn't have a say in anything," Smith says. Beset by anxiety, she began seeing a therapist who helped her realize she was being sexually harassed. Though she never filed a complaint, she left the job soon after and now works at a different nonprofit.

Still, despite the outcome — her former boss still texts and e-mails her — Smith accepts some responsibility for the role she played in the relationship. She relished the attention and enjoyed an "adrenaline rush" from their secret outings, she admits. "I'm not going to act like I was a helpless victim, although a part of me thinks I was," she explains, then pauses for a bit. "It didn't hurt me professionally. But I guess I was lucky."