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Advice / Succeeding at Work / Work Relationships

7 Places You Don't Want to Run Into Your Boss (Plus: What to Do When the Worst Happens)

When you get so used to seeing your boss at work, it can be easy to forget that he or she actually has a life outside the confines of your office. But, it’s true. Your supervisor has just as much of a social life as you do. Heck, she might even have more of a social life.

And, as the obnoxious Disney song goes, “It’s a small world, after all.” So, you should prepare yourself for the fact that you may eventually run into your boss outside of normal work hours. And, as luck would have it, that encounter might just happen in a somewhat uncomfortable setting.

Don’t believe me? Here are seven places you absolutely don’t want to have a run in with your manager, as well as how you should react if you do. However, fair warning: Nothing could make these situations less awkward. But, at least now you’re prepared for the worst.


1. Shopping (for Underwear)

Running into your boss while you’re out shopping is one thing. But, having to exchange pleasantries while you have your arms full of new underwear (or anything else you wouldn’t usually talk about at work)? Well, that’s just a whole new brand of awkward.

Before you ask, yes, this one was inspired by personal experience. My best advice? Just order your underwear online.


What to Do

If you’re able to spot your boss ahead of time, get rid of your purchases as fast as you can. Just put them down on the closest shelf and behave as if you’re browsing for something else. If not? An uncomfortable, “Hi, great to see you!” while avoiding direct eye contact and walking briskly past him or her will suffice.


2. The Gym Locker Room

You just suffered through your half-hour on the Stairmaster and are toweling off in the locker room. You breathe a sigh of relief that you managed to squeeze in your workout, when all of a sudden your boss comes strolling in. You both freeze in place and stammer for a minute, until one of you awkwardly says, “Oh, I didn’t know you go here!”

Now you’re stuck in the uncomfortable tango of deciding whether to change right in front of him or her or slyly shift on over to the bathroom stall. Spoiler alert: You can’t win.


What to Do

Well, considering you’re standing half-naked in a locker room, you likely don’t want to engage in a lengthy conversation about the quality of the gym equipment. Your best bet is to say something peppy like, “Great minds think alike!” Then pretend you need to go to the bathroom—and take all of your clothes with you. Next? You’ll spend two weeks stalking your gym to try to figure out a workout schedule that doesn’t overlap with your boss’. It will be well worth your time.


3. Drunk at a Bar

Whether you’re the drunken one or your boss is the person who’s completely inebriated, alcohol introduces a whole other dangerous element to this gauche scenario. After all, how are you supposed to look this person in the eye on Monday when you know she witnessed your slurred karaoke rendition of “Girls Just Wanna Have Fun?”

And, if you run into a tipsy version of your normally straight-laced boss? Well, it just feels wrong. It’s like thinking of your parents on a date. You know it happens, but you don’t want to be there.


What to Do

If you and your boss have already spotted one another, pull yourself together enough to say a polite, fast, and hopefully somewhat sober “hello.” If your boss is too buzzed to even notice you’re there? Settle your tab and run. Run like you’ve never run before.


4. Your Therapist’s Office

Sure, we all have things we need to talk through. And, visiting a therapist is a great way to do that! But, that doesn’t mean you want to sit awkwardly with your boss in the waiting room—especially when the only distraction from your uncomfortable exchange is a parenting magazine from eight months ago.


What to Do

Nod a simple “hi—what a small world!” and then pretend the parenting magazine is the most engaging read you’ve ever picked up. Absolutely don’t make a joke like, “I hope I’m not the reason you’re here!” It just won’t go well.


5. A Job Interview

You’re feeling prepped and ready for a job interview. You stroll into the company’s lobby with a spring in your step, and run almost directly into your manager. You both stop and give each other a confused look before launching into one of the most uncomfortable conversations of your professional life.

After your boss walks away, your mind immediately jumps to the worst assumptions. “Why is he here? Did he have a meeting? Does he know someone who works here? Did he find out I was interviewing, then set up a meeting with the hiring manager in order to tell her what a terrible employee—and crappy liar—I am? Yes, that’s definitely it. Now I don’t have any job.”


What to Do

Let’s face it—as soon as your boss saw you, he already knew why you were there. So, don’t bother explaining yourself right now. Instead, say a quick and polite greeting followed by a, “See you back at the office!” Then, take a deep breath and get back in the right frame of mind to ace your interview. (Or run and hide in the bathroom. The choice is yours.)

Then, read this article on what to do when you’re caught red-handed in the middle of your job hunt. You’re gonna need it.


6. At a Restaurant Alone

It’s Saturday afternoon, and you decided to grab some lunch at that great café around the corner from your apartment. You’re seated by the window innocently enjoying your turkey club and some Facebook stalking, when in strolls your supervisor—alone.

You make eye contact, and she comes over to greet you. You both keep awkwardly glancing at the empty chair across from you. Should you invite her to sit down and eat with you? Or, are you both going to eat at separate tables, doing your best to avoid eye contact?


What to Do

Sure, maybe you were intending on enjoying a quiet meal alone. But, your best course of action is to invite your boss to sit down with you. Worst-case scenario? She turns you down and tries her best to get a table as far away as possible. If not, you’re getting some extra time to connect with and impress her. Trust me, that never hurts!


7. Anywhere You’re Not Supposed to Be

You lied and told your boss that you needed Friday afternoon off in order to attend your grandma’s funeral. Come Friday afternoon, you run into each other in the bathroom line at the Mets game.

Being caught in a lie—especially by your boss—will always be uncomfortable. And, the only surefire way to prevent it is by, well, not lying in the first place.


What to Do

Well, there isn’t really much you can say to make it better right now. So, say hello and see where your boss takes the conversation. If he says something like, “We’ll talk in my office on Monday,” it’s time for you to drown your sorrows in some beer and peanuts. Or, just continue the lie by saying that your grandma’s funeral is actually at the Mets game—it’s what she would’ve wanted. That’s super believable.

No, but really, if you’re in this situation, you’re in big trouble. When you get home from the game (or wherever), you should sit down and write your manager an apology email along the lines of, “There’s no excuse for lying to you. While you’re understandably very angry right now, I hope that I can prove to you how much I care about this company by working harder than ever going forward.” Then, if you’re not fired, do that.



Even if you have a good relationship with the person who signs your paychecks, there will always be a few places where you absolutely don’t want to see him or her. And, while nothing can completely extract the awkwardness from those situations, responding appropriately should help—at least a little bit.

Or, you can opt to just never leave your house. That’s a viable choice too.


Photo of man with a bag over his head courtesy of Shutterstock.