When Petty Policies Backfire: How One Fiancé Outplayed His Future Wife’s Nitpicky Boss

There are few things more satisfying than seeing workplace pettiness get its just desserts—especially when the person serving them up is as smug as they are inflexible. If you’ve ever suffered under a boss with more policies than empathy, this story from Reddit’s r/PettyRevenge is your new favorite tale of poetic justice.

Meet our hero: a physical therapist who, alongside his lawyer fiancée, finds himself at odds with her notoriously difficult boss. What started as a simple act of kindness—a discount to his fiancée’s colleagues—soon blossoms into an opportunity to out-petty the pettiest man in the room. Trust me, you’re going to want to take notes for your next office showdown.

Let’s set the scene. Our storyteller (let’s call him PT Guy) is running his busy clinic while his fiancée navigates the shark-infested waters of law firm life. At their engagement party, PT Guy casually offers a discount to his fiancée’s coworkers—instantly becoming the most popular plus-one in legal circles. Four sign up as regulars, but eventually, the villain of our piece—her condescending, approval-hungry boss—books an appointment.

Right away, PT Guy sees what everyone’s been warning him about. The boss oozes arrogance and offers unsolicited opinions, but leaves his charm at the office. When the boss tries to cash in on the friends-and-family discount, PT Guy, with professional grace and a perfectly timed smirk, declines: “It’s for employees.” Touché.

But the real showdown is still brewing. During a later session, the boss learns one of PT Guy’s therapists is out sick. Instead of empathy, he pushes for a stricter medical certificate policy at his own office—believing, apparently, that paperwork prevents “slacking off.” PT Guy, ever the voice of reason, counters: Isn’t it better to let sick people stay home and avoid spreading germs?

Foreshadowing, anyone? Because soon enough, the universe does what it does best: delivers a cold to PT Guy and, unfortunately, his fiancée. She’s hit hard and has to work from home, then take a sick day. And just like that, her boss pounces—demanding, for the first time ever, a medical certificate to prove she’s really ill.

Now comes the chef’s-kiss moment. As fate would have it, the boss has an appointment at PT Guy’s clinic that very afternoon. But with his fiancée in need of a doctor’s visit (and unable to drive thanks to vertigo), PT Guy cancels the boss’s session, explaining that he’ll be busy chauffeuring his soon-to-be wife for her mandatory sick note. His schedule? Jam-packed for the next three weeks. Sorry, boss!

The cherry on top: The boss, suddenly realizing the consequences of his policy, frantically tries to call off the very requirement he enforced. But it’s too late—the wheels of pettiness are already in motion. The fiancée cites the clinic’s late cancellation policy (what goes around, comes around), and PT Guy insists on following through with the doctor’s visit. Irony, thy name is “strict sick note policy.”

Let’s break down why this story hits so many sweet spots:

1. The Petty Policy Paradox:
So many managers believe strict rules equal productivity, when in reality, they often backfire. Demanding sick notes for every sniffle? That’s a surefire way to clog up both doctor’s offices and employee goodwill—not to mention spreading more germs in the process.

2. Petty Revenge with a Purpose:
What makes this tale so satisfying isn’t just the snappy comeback or the schedule block. It’s that PT Guy stands up for empathy and reason—showing that sometimes the best revenge is simply holding a mirror to someone’s own bad behavior.

3. The Satisfying Symmetry:
The boss’s own policy ends up inconveniencing him directly. It’s poetic justice at its finest—a reminder that the rules you make for others can all too easily come back to bite you.

4. The Power of Saying No:
Whether it’s declining an undeserved discount or refusing to bend over backward for an unreasonable boss, sometimes the most powerful (and entertaining) move is simply sticking to your principles—with a little smirk for good measure.

So, next time you’re confronted with an inflexible policy or a petty power play at work, remember PT Guy’s story. Sometimes, the best way to win is to let people trip over their own red tape.

Have you ever out-pettied a petty boss (or coworker)? Share your stories in the comments below, and let’s celebrate those small, satisfying victories!


Reddit Source: I out did my fiancées petty boss


Original Reddit Post: I out did my fiancées petty boss