Answering Hard Questions During the Holidays

woman sitting at dinner table smiling during the holidays
Whether you’re visiting family or gracing the company Christmas party, awkward questions about your job, relationship status or personal interests are bound to come up. It’s best to be prepared.

Real-life holiday fun rarely runs as smoothly as “The Nutcracker” ballet. Really, when was the last time the Sugar Plum Fairies suffered an uncomfortable situation? In reality holidays are rife with awkward moments. They often start innocently enough. Like the time my family and friends celebrated around a table full of food while my children ran in and out of the room. Someone mentioned how great my kids were. I still regret my response.

“They are great. I’m just glad I didn’t wait to have them.”

It was a simple comment, but I saw my cousin pause and look away. I had forgotten that she wasn’t married, yet desperately wanted to have children. Forgotten that she didn’t know how God was going to work out all the pieces when she felt like she was left watching the clock. Forgotten that while she is incredibly happy, motherhood is uncertain for her.

I certainly didn’t intend to make her uncomfortable. If I had been thinking, I wouldn’t have said it.

Holiday Questions

As you gather with friends and family this holiday season, you may face some comments and questions that make you want to scream. A little anticipation and preparation goes a long way to minimize awkward moments (and it doesn’t involve getting new family or friends). Here’s help with three common questions you may face.

Question 1: Are you seeing anyone special?

Consider this: People often talk about what’s comfortable to them. For many people comfortable is being married by 30 with a dog and 2.5 kids. When they see someone on a different path, they may feel compelled to fix things. Or they could just be talking about what they know.

You have two main options here, and the route you take depends on what makes you comfortable. 1) You could lean in to the conversation. You could answer the question and talk about whom you are (or are not) seeing, what happened in the previous relationship or what you’re hoping for. 2) You could choose to pivot. Rather than enter into a conversation that makes you uncomfortable, turn the conversation toward something more agreeable: “Not right now, but I did see an amazing movie. Did you see it? The one with . . .”

It may sound cheesy, but a pivot works. It gives the person something else to talk about, gently shutting down the conversation for everyone. If the person brings up the same topic again, keep pivoting to new topics until they get the hint. It may feel a bit like dancing, but dancing is better than fighting.

Question 2: So do you have plans for the future?

Consider this: Back in the 1900s, the professional goal was to graduate high school, go to college, get a good job where you work for 30 years and then retire. That’s not reality anymore. In fact, it wasn’t always reality back then either, but it was a common expectation.

Let people get to know you better by offering your honesty rather than justifications. Maybe you love nannying or administrative work because it makes you happy. Or maybe you’re going back to school because you love learning. If you love being a barista, talk about why you love it. “It is great working with so many people every day. I love the connections I make, and bringing a smile to someone’s face is pretty great.”

It’s OK to say what you love about what you’re doing right now. You don’t need to apologize for enjoying the stage you are in. Similarly, you can say if you don’t love what you’re doing or if you’re unsure about it. Be confident in your answer. Maybe you hate making coffee. “I don’t love this job, but it works for now.”

Question 3: What are you up to these days?

Consider this: Most times this question simply reflects the other person’s attempt to connect with you and learn about your life, especially if he or she is in a different life stage.

Remind yourself that this is a conversation, not an inquisition. The more casually you answer without appearing defensive, the better the conversation is likely to go.

Giving a little thought ahead of time will help you smoothly negotiate this question. While you could talk about work or school, consider other options to bridge the gap between you and the one with the inquiring mind.

Share a few activities or interests you have going on or that you like to talk about. Maybe you’ve been exploring some art galleries; talk about pieces you love. Perhaps you’re part of a Bible study; share about the group or the book you are studying. Then ask if the other person has recently read any interesting books.

Uncomfortable questions and awkward moments don’t have to turn anyone into a grinch during the holidays. With some anticipation and a light touch, you can deck the halls with grace and cheer.

Copyright 2018 Rebecca Hastings. All rights reserved.

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About the Author

Rebecca Hastings
Rebecca Hastings

Rebecca Hastings is a writer and speaker who encourages women to find hope in all the good, messy and real parts of life.  A wife and mother of three in Connecticut, her book, “Worthy: Believe Who God Says You Are,” is available on Amazon. You can read more from Rebecca at

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