How to Ditch a Firm Fling

Matthew Richardson Columns, Lawyer 27 Comments

Dana, the voluptuous 23-year-old paralegal I was banging, asked me to talk dirty to her one night. I’m not a fan of dirty talk. But as I whispered not-so-sweet objectifications in her ear, I realized that not only did I not want to talk dirty to her, I didn’t want to talk to her ever again…period. Unfortunately, that can be a tricky order when the person you’re using for sex is also the person you rely on using for legal research.

I know you’re not supposed to dip your pen in the company ink, but you’re also not supposed to pad your billable hours, use your Lexis account to do background checks on your friends or leave the office mid-day for a visit to an Asian massage parlor. Those may be rules you live by, but not me. I like to think of those things not as rules, but as naughty enhancers.  When an act—take sex with a co-worker, for example—is forbidden, chances are it will feel great. Better than any condoned sex you could imagine. 

But when the time comes to say farewell, you need an exit strategy. 

But, Matthew, how do I ditch a co-worker without a huge scene at work…or getting fired?

The only way you’re going to find a solution is to ask yourself, “WWUAGD: What would the ‘Unethical and Amoral’ guy do?” And the answer depends on one cursory question: What garden-variety rank does that person hold at the firm?

Each inter-office romance coup de grâce requires knowing who you’re dealing with.  The warning label for blowing off a secretary reads differently than breaking up with a partner.  The only similarity: It won’t be pretty.  But if you remain strong and stay the course, you will likely soon find yourself off the hook and eligible to go back to the inkwell for an entirely new naughty-enhancing dip.


In the balance of power between an associate and a secretary, you have more to lose.  The more the secretary exposes the situation to others, the more you’re perceived as a predator while she soaks up undeserved sympathy. That means common spaces in the firm are to be strictly avoided when edging out the secretary.

Trust me.  My first secretary was a passable redhead I banged two weeks after joining the firm.  But after a few late nights, I wanted off the welcome wagon.  She could have stormed into my office and pitched a fit, but that wouldn’t have been satisfying enough for her—no audience there. So where did she choose to confront me about the cold shoulder I was giving her?  The cafeteria. 

Think back to your days in high school and ask yourself where you saw the nastiest breakups. The ones between the varsity athlete and the vulnerable freshman.  The relationship may have hit the rocks at a party, but chances are that it all went to hell over cold tater tots and orange-slick greasy pizza in the cafeteria. Why? Because a jilted lover needed a spectacle, and the high school cafeteria (or your firm’s lunchroom) offers the most bang per buck in audience size. And not just any audience, but an audience that’s just familiar enough with you to ensure that any sort of relationship meltdown goes viral before you put down your knife and fork. 

I learned my lesson—order in, go off campus, or tell your paralegal to make himself useful and get you a sandwich, but avoid the cafeteria at all costs.

When she notices you’ve eliminated firm fixings from your diet, she’ll resort to trolling for you in the hallways.  So for an extra veil of separation, keep you office door closed.  Firm has an open-door policy?  Screw it.  If you were going to play by the rules, you wouldn’t have banged a secretary in the first place. There’s no f**king hall monitor, and even if someone does say something, do you really think HR is going to chew you out for a closed door? They’ll make you open it, that’s all. Play along, prop the sucker open, and then close it when the HR chick goes back to her Cruller collection.


Two rules when cancelling the paralegal: 1) Increase workflow; 2) decrease facetime. 

I once banged a paralegal who worked in the bullpen across from my office. Know how I sent her the message that we’d never, ever speak again? Interoffice mail, that’s how. I sent her 22 separate documents the day after we broke up—all of them via interoffice mail. It’s cold and impersonal, and that’s exactly the point. Going out of your way to avoid someone and creating extra paperwork for that person in the process is a great way to make it clear that you don’t want to see them.


The summer associate is the most fragile of all, so kitten gloves and an emphasis on secrecy are musts. 

It doesn’t take balls to hookup with a summer. But it does take balls to deal with the aftermath. Let’s face it, not everyone can take a hint—especially newly minted 3Ls looking to score a downmarket offer at all costs. So if you must speak to the SA in question, use their inability to grasp the obvious to your advantage.

For me, verboten summer associates are entirely irresistible. I once hooked-up with an SA who was as clueless as she was hot (some kind of correlation there). She didn’t get the obvious hints, like not holding the elevator door for her and blatantly turning the other way when I saw her walking down the hall. But I didn’t let her clueless behavior suck us both into a full-blown relationship. Instead, I pulled her aside and said, “We can NEVER, EVER talk in the office. In here we have to be SECRET FRIENDS. This is to protect my reputation and YOURS. You don’t want to be known as the woman who slept her way to an offer, do you?”

With that pack made, you then must pray like hell and do everything in your power to secure them a spot at the firm.  Once that’s locked in, you’re good to go. My girl got the offer and still works here to this day, but we haven’t talked since. And it’s been three years. 


I’ve tried every trick in my book on this one, but staff attorneys are different.

When you’re dealing with an especially hot, borderline-psycho co-worker, like the staff attorney I banged back in ’07, you’ll need to resort to puling ranks. Staying off the partner track may keep inches off their waistlines and pounds off their asses, but there’s a reason their careers are stuck somewhere between “hopeless associate” and “worthless paralegal.”

In the case of the staff attorney I banged, the reason I needed out was that she was a crazy-ass b**ch. Hands down, she was the best BigLaw lay I ever had, but shaking her loose required a little something extra.  When we were both alone, I had to lay down the law, telling her that if she even mentioned that we had shared a drink (let alone bodily fluids) to anyone, I would see to it that she was fired. 

Did you have the power to do that, Matthew?

Of course not.

Could she have sued you and the firm?

You bet.

Did she?



Because I’ve got pictures of her dressed up as a naughty nurse on my computer, and even a brain-dead staff attorney knows those will somehow find their way out during discovery.


In the hierarchy of avoiding co-workers you’ve defiled, the most complicated act to shake is someone who can order you around—the lonely female partner. You may have told her to bark like a dog at your apartment, but at the office, she’s top dog.  And that requires an accomplice to effectively duck. 

You can usually brush her off by having your secretary (preferably one you haven’t slept with yet) tell her you’re on a call when she drops by or pretending that you have a meeting. Do that enough times, and lonely female partner will get the hint and move on to some other associate sleazy enough to play cub to her cougar.

But everyone once in a while, you a get a cougar who isn’t in the mood to hunt for anyone else but you. In that extreme case, the only thing to do is call for backup. You need to use another partner as a shield, and that means taking on more work—which is obviously never ideal in my universe. When you refuse to take her calls or emails, she will be forced to ask the other partners what you’re doing. For once, they can honestly say that you’re swamped.

None of these are perfect solutions, but they are at least guideposts for life in the wild BigLaw sex kingdom. Think of me as your WWUAGD safari tour guide. 

Matthew Richardson is mergers & acquisitions by day, Unethical & Amoral by moonlight.

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  • Katzenbach

    Very good advice.

  • ex bl3y

    this post makes it clear to me that matthew richardson is full of crap (and i don’t think commenter 1 has ever been laid, are you even out of high school?)
    regardless of how crazy you think a woman is, there is always a graceful way to exit, unless you a) are socially awkward and uncomfortable in everyday situations, b) are a douchebag with zero self awareness and/or c) never learned how to convince a lady that what you want is what you both want (which means you’re probably a lousy lawyer too).
    i know this post is just a sorry attempt to get a rise out of undersexed lawyers and law school (high school) students, but at least stick to what you know (like prostitutes, strippers and the chick behind the starbucks counter that won’t give you a date).

  • ex bl3y

    i guess they deleted the first comment (i didn’t mean you Katzenbach, but you’re obviously a social retard as well).

  • Anonymous

    this string of notes is boring.  Matthew rocks!

  • BL1Y

    When I was an SA, I got really trashed at a firm event after party and hooked up with a midlevel associate.  I was so drunk that I was still messed up in the morning when I left her apartment.  To this day I don’t know who it was, or if she even still works at the firm.  I don’t recommend it.

  • The Truth

    BL1Y: I think you’re lying.

  • Anonymous

    Why would he lie.  I boned a 5th year when I was a summer associate.

  • BL1Y

    If I was lying, I’d have said she was attractive.

  • Idiom police

    “so kitten gloves and an emphasis on secrecy are musts.”
    Do you mean “kid gloves”?  What are kitten gloves?  Sounds illegal…

  • Internal Affairs

    @ Idiom Police,
    Try Google. First entry for “kitten gloves” is Urban Dictionary.
    Usage seems proper to me.

  • BL1Y

    And after looking at Urban Dictionary, you should look at the rest of the top Google results, and realize that the person who put it into Urban Dictionary probably got the phrase wrong, just like how some people will say “for all intensive purposes,” “raft race,” “labtop computer,” or “French benefits.” Eventually such a mistake can become the new phrase (such as with “hocus pocus” from “hoc est corpus”), but I don’t think “kitten gloves” has reached that point.

  • Craig

    Let me add one more to BL1Y’s list that always make me laugh. When people claim a point is now “mute.”

  • Craig

    I can see using the phrase “kitten” gloves here, which is a baby pussycat. The reference was used to describe how to deal with young summer associate puss, er, women that you had sex with.

  • Anonymous

    I guess BL1Y has little discretion.  He will point his peter meter anywhere that will have it.

  • Anon Female

    Pretty darn funny. great reading.

  • BL1Y

    I prefer the joke from friends, “It’s a moo point.  Moo, like a cow’s opinion, it doesn’t matter.”

  • Anonymous

    Thanks for the very good advice.

  • Anonymous

    Not bad. Good advice on how to dump a broad after she’s outlived her usefullness.  It’s the American way, mahn!

  • BL5Y

    hilarious!  I might be able to use some of this to dump that partner I’ve been sleeping with.

  • Nigel B

    Interesting, but will this advice really work for the in-house tools who realize they too need to move up from the bovines they’ve been drilling at work?  When you only have 1 corporate client, there is a lot more at risque, I would think.

  • miserable associate

    i wish i saw a secretary worth boning at my office ever…btw- do attorney’s eat in the cafeteria? thats pretty bush league. you dont mix with the commoners.

  • AllLawyersSux

    To Miserable Associate:  I can see why you’re miserable!  You must work at some irrelevant firm with a staff of 50 at the very least!  HA.  Get out and venture, Son!

  • Content Associate

    I agree with the Miserable Associate, while I enjoy my job, there is not a paralegal or secretary worth banging in our office.  And, no, a lawyer should never eat in the cafeteria with the help.

  • Hannah Palindrome

    QUIT HAVING SEX with your secretary, paralegal, summer associate, etc.

    Call/In/Out/End of Drama

  • none of your

    how do i dump the lawyer who wants me but still keep him on my case, not ass?

  • still none of your

    Sometimes, it does go the other way, ya know.  Lawyers are eminently dump-able, too.  Male lawyers.  Sorry to burst your bubble.  Head.

  • Human Resources

    Does the name Palden Namgyal ring a bell?