8 Most Scandalous Work Affairs

A list of the most scandalous work affairs, how they started, and their aftermath.

male coworker touches woman's rear

Workplace romances are hardly uncommon. After all, you're probably clocking in more hours at the office than at home. It's easy to develop close on-the-job relationships that can take a romantic turn. Excelle: Love Conquers All Workplaces

But what often starts as a titillating romp in the supply room can quickly turn into a train wreck, endangering your career and your future.

Are you willing to chance it? If so, you're not alone. Celebrities, politicians and high powered executives have been known to risk everything for an on-the-job fling.


1. Bill Clinton & Monica Lewinsky

The Frolic: Unless you've been living under a rock, you survived "Monicagate" and know what led to the impeachment of an American president. So let's hit the high notes, shall we? President Bill Clinton vehemently denied having sexual relations with White House intern Monica Lewinsky after Internet gossip column Drudge Report broke the scandal online. A bold-faced denial under oath—backed by taped conversations of the alleged affair—ended in an impeachment trial and obstruction of justice and perjury charges. Clinton dodged the bullet and remained in office, leaving with the highest approval rating of any president since World War II.


The Fallout: In the months after the dust settled, Lewinsky made sure to milk her fleeting fame for all its worth, making the morning show rounds, helping pen her side of the Clinton affair, appearing in a Saturday Night Live skit, and shedding weight for Jenny Craig. After an unsuccessful stint as a handbag designer, Lewinsky fled to London where she pursued a master's degree in social psychology. As for Bill, I think he's doing all right.

2. Newt Gingrich & Callista Bisek

The Frolic: Back in 1998, Newt Gingrich was all over then-President Bill Clinton for his moral weaknesses, leading the charge to impeach Clinton for getting it on with a much younger intern. After a long day of cheerleading Clinton's crucifixion, the then-Speaker of the House went home to the comforting arms of his... mistress. Yep, the leader of the family values pack was seeing Callista Bisek—a woman 23 years his junior—behind his second wife's back. Pot, meet Kettle. He eventually made an honest woman out of the blonde staffer but kept their near two-year adulterous affair on the down low. Excelle: 4 Ways Employers Could Help Our Relationships

The Fallout: Those in glass houses should never throw stones. In 2007, the über conservative admitted to wooing his now wife while he was still married, but saw his extracurricular activities as far from hypocritical. After all, Clinton was impeached not for having an affair but for lying about it. The spin seemingly saved his career. The Fox News analyst is reportedly considering a run for president in 2012 with his former fling at his side.

3. David Letterman & Female Staffers

The Frolic: The talk show king uses sexual liaisons as fodder for late-night laughs, so when personal indiscretions came to light, the comic defaulted to what he knows best: jokes. Letterman's casual confession to romping with female staffers stunned his audience, but it didn't close the curtain on his career. Instead, his 10-minute monologue stopped a former producer from extorting $2 million to keep the affairs secret. In an industry where timing is everything, the gap-toothed comedian focused on the would-be blackmail to help take heat off his own dalliances. Instead of apologizing for cavorting with employees and cheating on his wife (whom he dated for 23 years before marrying), he painted himself the victim of a cruel scam. Way to spin it! Excelle: Dating A Coworker: Can It Work For You?


The Fallout: Not much. Letterman's ratings have never been better (up 22% over his average at the same time last year), his blackmailer is behind bars, and his wife seems to have stuck around for the sake of their five-year-old boy. A spokesman for Letterman's production company said its policy doesn't ban booty calls between managers and employees. Looks like he'll continue to make potshots at fellow philanderers and get off scot-free. There's nothing a top ten list can't fix!

4. Steve Phillips & Production Assistant

The Frolic: A well-known sports celebrity recently checked out of a secluded sex addiction clinic. And no, it wasn't Tiger Woods. Former ESPN analyst Steve Phillips is busy picking up the pieces after a tryst with a production assistant wrecked his career and nearly destroyed his marriage. Phillips had hoped his alleged three-night stand in July 2009 would fly under the radar, but 22-year-old Brooke Hundley was a bit more smitten. After Phillips cut her off, she allegedly cyberstalked his son on Facebook and harassed his wife with calls and a letter, describing Phillips' birthmarks and details of the dalliance. The cable giant initially suspended the baseball expert but decided to fire both parties after the scandal went public. Phillips immediately entered the same Mississippi clinic as Woods to get therapy.

The Fallout: After spending a month and a half in sex rehab, Philips immediately hit the airwaves on damage control, publicly apologizing on The Today Show and vowing to save his marriage. If he’s successful, it won’t be the first time his wife has forgiven his flings. He admitted to having extramarital affairs with several women during his stint as the Mets general manager (1997-2003) and was threatened with a sexual harassment lawsuit in 1998. He hasn’t said whether he’ll return to broadcasting. ESPN made no public statement regarding the issue.


5. Brad Pitt & Angelina Jolie

The Frolic: How do you relax after a tense day of car chases and shootings on a movie set? Why, by cuddling with your costar in your trailer, of course. OK, that may not be exactly how two of the world's most beautiful people hooked up, but Angelina Jolie admits she fell for then-married Brad Pitt while on the set of Mr. and Mrs. Smith. Their onscreen chemistry kept us on the edge of our seats so we weren’t too shocked to hear they'd shacked up after the cameras stopped rolling. Jolie claims she kept her distance until Pitt divorced his then-wife of five years, Jennifer Aniston. Pitt just happened to file those papers that same year. Hmmm.

The Fallout: Tabloid magazines owe a good portion of their revenue to steering the Angie and Brad breakup bandwagon. The gossip mill churns out a separation story every other week but the pair—who've never been officially married—are seemingly still going strong. Not just a pair of pretty faces, the charitable couple are attached to several humanitarian causes. In 2006, they established the Jolie-Pitt foundation to aid in global causes. Most recently, the foundation donated $1 million to Doctors Without Borders to help victims of the Haiti earthquake.

6. Ad Exec & Ad Exec

The Frolic: Sex may not always sell... but it sure spreads on the Internet for free. In late 2008, two New York advertising executives became infamous online sex stars after a tape of the two having sex on the office floor went viral. A co-worker who stumbled upon the cubicle coupling alerted his buddy, who then taped the after-hour sexcapade. So how did a 60-second cell phone recording sent to a few office colleagues end up on Gawker.com and in thousands of inboxes? That’s the magic of the Internet.


The Fallout: Apparently taping the act is worse than doing it, to HR anyway. The company fired the voyeur for recording the fornicators (both reportedly married and one high up on the company ladder) but the two unnamed execs have kept their jobs. Mad Men producers must be proud.

7. Saudi Arabian Man & T.V. Viewers

The Frolic: To ere is human, but keep it behind closed doors if you live in an ultra conservative country. In 2009, the Saudi Arabian government pulled the plug on a Lebanese broadcaster operating in the Kingdom after a lewd episode sent viewers scrambling for the remote. When producers of The Bold Red Line asked a divorced airline employee on as a guest, they had no idea he'd single handedly bring down the popular talk show by spewing erotic foreplay talk, a detailed aphrodisiac recipe, a recap of his personal sexual exploits and even a sex toy demo. Producers claim they edited the video to show the least amount of naughty bits, but still gave the lascivious chat fest a green light. Unfortunately, it wasn’t kosher suppertime entertainment for this strict Muslim kingdom.

The Fallout: In a country that enforces strict segregation of sexes and deems making love outside of marriage illegal, sexual immoralities rarely see the light of day. Air your dirty laundry and face a stiff punishment. The father of four is begging for forgiveness behind bars after being charged with "publicizing vice." He could face 20 years in jail or even death. However, his attorneys aim to sue the station over misrepresentation. Meanwhile, the station itself is struggling to reinstate its operating license.


8. British Envoy & Prostitutes

The Frolic: Russian intelligence agency sets up sex sting. Prostitutes lure British diplomat into hotel room. Recording equipment tapes sexual activity. Video leaked on the Internet. Britain shamed. Envoy resigns amid scandal. No, this isn’t a sneak peak at the next James Bond film. In 2009, Deputy Consul General James Hudson was allegedly caught in a "honeytrap" and taped having sex with two Russian hookers. A link to the 4-minute video clip, titled "The Adventures of Mr. Hudson in Russia," was immediately posted on a Russian news site.

The Fallout: Hudson never admitted to whether he appeared in the video, but he resigned his post soon after the scandal broke. Outraged British officials accused the Russians of staging a sting to either blackmail Hudson or embarrass the country. Russian security services are known for masterminding such operations and British officials routinely warn their envoys of frequent entrapment attempts.

Lessons Learned


So how do you refrain from following in these (in)famous footsteps? Follow these five simple rules and you'll stay employed and out of trouble:

  • If you stray and are caught, fess up! Lying about it will only make things worse.
  • Know your companies HR policies, especially if you are in a management position.
  • Stay away from married coworkers, duh.
  • Understand the risks involved, and make sure you're willing to face the consequences.
  • People will ALWAYS find out. If you think you can keep this under wraps, you're kidding yourself.

Written by Nealeigh Mitchell for Excelle