Hardly a week goes by when we don’t see the words “sex,” “scandal,” and “lawyer” arranged together into some irresistible headline. While we love reading about lawyers behaving badly, one thing that continues to stump us is why a group of seemingly intelligent, obviously well-educated professionals appear to have such a knack for getting caught with their pants down.
Just look at national news stories from this month to get an idea of what we’re talking about:
- The dean of Villanova law school, Mark Sargent, was forced to resign after authorities allegedly busted him for being a customer of a brothel. [[Los Angeles Times]
- And then there’s always former New York governor Eliot Spitzer, who has been on a media blitz ever since the economy hit the skids. Sadly, most people still think of him as Client #9, which is too bad because there are certainly good opportunities these days for regulators who have a reputation for being tough on Wall Street. [Reuters]
But should these guys have really been caught? We think not. And let’s face it, it’s not easy finding favor once the forbidden is exposed. “92% of Americans said married men or women having an affair is morally wrong.”
So we’ve compiled some tips to help you keep your naughty business private. And before you go calling us sensational, it’s worth noting: Sex happens. A January Bitter Poll concluded that half of you assume that more than 25% of married lawyers are having affairs.

Not to mention the number of reader-submitted questions that keep Ex-Bitter busy dispensing experienced advice on everything from “I Did Coke and Slept with a Paralegal” to “I Made Out with a Married Associate.”
We make no promises these are foolproof, but they’re all steps in the right direction to staying under the radar. Consider this a public service announcement from Bitter Lawyer.
Say “NO” To BigWhore
Every lawyer wants that golden offer from a white-shoe firm. But when you’re the one giving the offer—in this case an offer of cash for sex—make sure you’re retaining a solo practitioner. In February, we profiled the similarities between hookers and lawyers. Each woman we spoke with told us this simple fact: Had Eliot Spitzer not used an escort service, he would still be governor today.
When we spoke with Veronica Franco, a Los Angeles-area escort, about that story, she told us that independent providers don’t attract very much attention from law enforcement. “If you’re a vice cop, you go for the big prostitution rings,” she told Bitter Lawyer.
Translation: If you must use a hooker, make it a one-on-one transaction.
Cases in Point:
- “Lawyer arrested in Tampa prostitution sting” [St. Petersburg Times]
- “Prostitution sting in West Des Moines nets lawyer, pastor” [Des Moines Register]
- “’More Names Will Come Out,’ Lawyer in D.C. Escort Case Vows” [Washington Post]
- “The Spitzer Scandal: Lust Plus Pride” [Time]
Lazy or Crazy?
When we asked “Jane,” an escort who blogs at Debauchette.com, why so many men get caught with escorts, she chalked it up to two simple reasons: Self-destructive or lazy.
While we can’t offer much help to the guys who want to get caught, Jane did recommend that people engaging in illicit activities take basic security precautions. Calls from work phones and emails from business accounts are “surprisingly common,” according to Jane. Fortunately, the solution is an easy one—sign up for a free email account, and for goodness sake, don’t use your real name. Oh, and don’t book a “date” from your office phone.
Cases in Point:
- “US Senator sorry for prostitution links” [ABC]
- “A Company Computer and Questions About E-Mail Privacy” [The New York Times]
Holler on Your Own Dime
Q: How do criminals get caught?
A: With their cell phones.
Q: How do we know this?
A: We read it in The New York Times.
Like it or not, Big Brother is here. So if you really value your privacy, and you can’t resist doing something naughty, plop down the $30 for a pre-paid cell phone (hobby phone, shag phone, dirty phone, textyback). Just remember to use cash for your purchase, and while you’re at it, pick up one of those pre-paid credit/debit/gift cards for when you need to add minutes.
Cases in Point:
- “Private Eye: How Spitzer Could Have Gotten Away With It” [Laptop Magazine]
- “Wiener wants phone records in prostitution case” [Associated Press]
- “Do cell phones cost more than prostitutes?” [CNET]
Surf in Style
This one wouldn’t have helped Judge Kozinski because he actually hosted adult content on his server when he could have just visited millions others. But when we asked our computer tech from HyperNerd how we could check out porn without getting caught, he gave us this sage-like advice:
First, designate a separate Internet browser exclusively for all of your illicit queries. Use it only for your down-low penchants. Don’t leave a shortcut for that browser on your toolbar or desktop because anyone who uses your computer will be just a click away from your porn stash.
Second, make sure you disable the cookies on your “adult” browser. You should also regularly clear the cache and operate the browser in its “privacy” mode. If you use Chrome, our tech’s favorite choice, you’re looking for something called “Incognito Mode.” In Safari, it’s “Private Browsing” mode. It prevents any information from being written to the cache, download manager, history manager, or login manager. It will also clear all cookies and will not prompt you to save any passwords during your session. Explorer, Firefox and Opera all have similar porn-friendly modes.
Our tech guy also pointed out that if you use Microsoft’s new search engine, Bing video, with the “Safe Search” filter off, you’re one errant mouse move away from finding your perversions without visiting a single objectionable site. Why? Well, unlike other search engines, Bing’s video results autoplay when you mouse over them. (Suppose a good lawyer would question the possible copyright snags this presents, but that’s not the point.)
Cases in Point:
- “Officer accused of viewing porn at work” [Wane.com]
- “Strong Dissent in Porn-Related Computer Search Case” [Law.com]
- “Microsoft Internet Explorer 8 to Include So-Called ‘Porn Mode’ Privacy Feature” [Fox News]
- “Microsoft Bing Porn Content Gets Its Own NSFW Domain” [Gizmodo]
No Glove, No Love
Remember Frederick Tanne, the Kirkland & Ellis partner who sued his ex-wife, her lover, and anyone she ever met because he thought she gave him herpes? Well, even though Tanne was wrong about who gave him the herpes, his case provides a valuable lesson for all. If you’re going to cheat, use protection, because nobody wants to be busted by a burning sensation and a trip to the doctor’s office.
Cases in Point:
- “Manhattan Lawyer Wrongly Sues Wife for Giving Him Herpes” [New York Post]
- “Saturday Night Live Valtrex commercial featuring Alec Baldwin” [NBC.com]
- “Affairs and STDs” [Families.com]
Hush the Gush
Is the love of your dreams (your “soul mate,” so to speak) not the person you’re married to? Resist the urge to leak that you’re mad for your mistress. Check yourself: It’s your hormones talking. It’s probably even the Girlfriend Experience* talking.
“New” and “exciting” rarely means you’ve been shot by Cupid’s arrow. Instead, breaking this rule can get you shot down by the public and incriminated. Or worse, just plain shot. It’s not a love story, so keep the intense romantic feelings to yourself. And make every effort to ensure the other half keeps a lid on it too.
*”The precise definition of GFE is murky, but according to the escorts, the term is a catchall for a more-personal touch, including kissing and cuddling. The experience is meant to combine the punch of great sex with the emotional connection—albeit for a limited time—of a relationship.”
Cases in Point:
- “Sanford admits more visits with ‘soul mate’” [The Philadelphia Inquirer]
- “’Soulmate’ Madonna” [Boston.com]
- “Lewinsky: He Was ‘My Sexual Soulmate’” [CBS News]
Find a Partner in Crime
People cheat. It’s a fact. And while there are plenty of fish in the unfaithful sea, it pays to cast your line away from work, your friends and the long arm of the law. At least, that’s what former lawyer Noel Biderman told us back in January when we interviewed him about AshleyMadison.com, a dating site for the unfaithful among us.
“What we are saying is that if you have decided to step outside of your relationship, don’t have an affair at work and risk losing your job as well, don’t go on a singles-dating site and lie about your marital status, and don’t break the law and seek out a prostitute.”
That’s good advice. But you, of course, have to pair it with some of the tips we just gave you. Call your partner in crime with a pre-paid phone, pay for hotels with a pre-paid credit card, and let Benjamin Franklin pick up the tab when you go out. And if you don’t think that’s good advice, walk down the hall, find the nearest divorced partner, and run some of those ideas by him or her.
Cases in Point:
- “Michiganders flock to Web site for flings with married cheaters” [Detroit Free Press]
- “Ashley Madison.com … Good for Business?” [One Law Blog]
- “Lawyer’s Affair Leads to Firm Breakup, $2M Verdict” [ABA Journal]
- “Lawyer’s affair with murder trial witness” [Daily Mail]
Don’t Fall Into the Dark Side
The attorney/hooker commonality of “We both screw people for money” can sometimes confuse lawyers as to what side the sexual agreement they’re representing. Regardless of how lucrative it may seem, leaving the law to be a sex outlaw usually comes back to haunt you. Several lawyers have tried using their training to be a madam, escort or pimp, and it’s usually a matter of time before we wind up reading about them.
Cases in Point:
- “Former US law student who became escort pleads guilty to tax evasion” [Guardian]
- “Former escort and Stanford law school grad having trouble meeting terms of plea deal with feds” [San Jose Mercury News]
- “Ex-Prosecutor Is Accused of Running Escort Service” [Law.com]














