How to Deal When Your Coworkers Ask Awkward Questions


Coworkers talking


Kaitlyn Duling
Kaitlyn Duling63

If it hasn’t happened to you yet, it will. You’ll be innocently, comfortably lounging in the break room, kitchen or another shared space. You’ll be sitting on some furniture designed to be “fun and functional” that has started to show its age, unfortunately, and the one thing that you never thought would happen, will happen. Your workplace will transform from the idyllic, easy, social paradise you thought it was for the first month (or week, or day…) you worked there, and turn into its truest form: a haven for colleagues and bosses who ask extremely awkward questions.

This will happen. Nothing is pure. So how do you deal? There are a few options:

1. Be shockingly honest. This is the quickest way to make your colleague just as uncomfortable as you are. The next time you hear “You don’t look so good this week. Have you showered?” go ahead and tell them all the gory details of your sinus infection, period cramps or stomach flu. “Are you pregnant?” can be easily met with “Oh, no, but I do wish I was, and we’ve been trying, and if you have time it would really help to talk to someone about it.” The more honest you can be, the better. Go ahead, share how you got that weird rash. Questions about family? Money? Yep, if you let them have the dirty details, even just once, I promise they’ll never ask again.

2. Change the topic entirely. “Don’t I want to make American great again? You know, funny you asked, because I have been thinking about getting a standing desk, and I really can’t decide if it would improve my core muscles all that much…” If you don’t want to talk about it, don’t.

3. Throw it back at em. Sometimes honesty can be used to do more than just push people away. If you love your job 99 percent of the time and would like to continue happily working there, try giving yourself a couple deep breaths—and then answer the question, honestly. Even if it makes you a little uncomfortable or causes you to blush at first, being radically forthcoming can often build trust. It can be easy to become a little too private at work, operating in our own little zones. This can make us seem stuffy, unapproachable, and like we’re holding something back. Don’t hold back! You don’t have to tell anyone your life story, but the next time the woman sitting next to you at lunch asks if you’ve been through a breakup lately, you can say “Yes.” You can even say “Yes, and it was hard, but I’m doing better now.” And if you really want to build that workplace friendship? You can go ahead and ask her, “Have you?” (That’s probably what she really wants to talk about, anyway.)

4. Raise those eyebrows to the sky. Sometimes the awkward questions asked by colleagues aren’t just quirky; they’re shocking and potentially even offensive. As an out lesbian in the workplace, I’m often asked invasive questions about my personal life and sex life, usually by people I hardly know. If you feel surprised and uncomfortable in a conversation, it’s entirely valid to express that discomfort. I like to react naturally: “Excuse me? I can’t believe you asked me that!” or even “Wow. Why would you ask that question?” When paired with a look that mirrors the disbelief and disapproval I’m feeling inside, this reaction can be the ultimate conversation-ender. No one ever wants to feel like they’ve said the wrong thing. But sometimes, unfortunately, people do. And it’s okay to let them know that it's made you feel awkward.

If you’ve tried all of these options, and your cube mate still insists on asking about your salary, sex life or spiritual beliefs and makes for awkward moment after awkward moment, you might just have to give them the silent stare and frown. Or make a rule—more than once, I’ve let coworkers know that I don’t like to discuss money with people who aren’t close family. Remember: Any conversation is half yours, so you get to help make the rules! Don’t be bullied into answering questions that you’d rather not discuss. Of course, if you feel really uncomfortable, in that icky-no-good-gross way, tell your supervisor. No one should be forced to have an upsetting or disturbing conversation. Just awkward? That can be okay, especially if you have some textbook responses lined up. Next time, you’ll know how to deal.


Kaitlyn Duling is an author and poet who is passionate about supporting and uplifting other women. Her work can be found at