Skip to Content

How To Answer Awkward Questions During The Holidays

Parties are fun. Those uncomfortable questions are not. Here's how to answer them!

The holiday season is a favorite for many; parties with family, friends, and work colleagues are often a staple. Socializing with others around you can be fun, but by the same token, it can also be a daunting prospect, especially because there is always the chance that you’ll be asked to answer awkward questions during these gatherings, regardless of your companion’s intentions.

Some awkward questions you might be asked during the holidays are:

  • How’s the job search coming?
  • So when are you having kids?
  • Why don’t you have a boyfriend/girlfriend/partner yet?
  • When’s the wedding?
  • Still working at the same place?

… and on and on. We’ve all been in these awkward situations before, having to answer probing questions from strangers. Try to remember that most people are just making conversation, they don’t necessarily mean to be rude or nosy.

Although I am by no means an expert in the art of deftly maneuvering your way out of an awkward question, I have developed a few tried and true techniques that have allowed me to escape a potentially awkward situation unscathed during the holiday season.

Here are four tips to answer awkward questions this holiday season:

Tip #1: Plan Your Answers (Or the Gist of What You Want To Say) Beforehand

 I’ve found that if you have a general idea of who you might encounter or the questions some people may ask you, it’s a good idea to anticipate potentially awkward questions by deciding how you may want to answer some of the questions they may ask you, and maybe even practice a bit on our own prior to the event if necessary. Think of ways you might be comfortable answering questions that might be potentially awkward, and formulate some basic answers in your head prior to the event. 

My family and I recently attended a holiday event where I encountered a few potentially awkward questions about my current work situation and job search. However, because I knew several individuals who would most likely be attending the event, I was able to take some time to think about how I wanted to answer the questions they could ask me. This doesn’t mean that I spent the days leading up to the party obsessively memorizing answers and recited the answers to these individuals’ questions like a robot; rather, I simply decided what I was comfortable telling these individuals, and the basic structure of some answers to potential questions.

You have no way of anticipating exactly what sorts of questions you may be asked or how they may be worded, so I found it most effective to prepare by having several stories, answers, or even questions for your companion, in order to make sure the conversation runs smoothly, just as you would practice for a job interview or an elevator pitch during a networking event.

Tip #2: Ask Questions and Listen

I have found that one of the most effective ways to avoid uncomfortable questions within communication is to ask questions of whoever you are speaking with. It gives you a chance to listen to others, and shift the attention away from yourself, especially if that makes you uncomfortable. Turning the tables and asking questions of others is also a great way to learn more about the people around you, and you never know what you may learn, not just about the people around you, but also about the world around you.

The conversations that I had with several individuals during these holiday gatherings allowed me to learn things about these individuals that I had never known previously. Moreover, I was pleasantly surprised and grateful to have offers from several of those individuals to connect me with others who could potentially help me by the end of the night.

You never know what you may learn or gain by asking questions and listening to those around you; you may be pleasantly surprised, just as I was.

Tip #3: Determine When You’re Going to Leave The Gathering Beforehand

 Although this isn’t necessarily strictly a holiday party thing, I’ve found that something that helps me, especially if you find holiday gatherings overwhelming or intimidating, is to determine when you’re going to leave the party before you even arrive at the gathering. This will give you a definite timeframe, and something to look forward to should the party get too overwhelming for you.

Moreover, having a definite time frame will allow you to keep the conversations short and sweet; this doesn’t guarantee that you’re going to avoid awkward questions, but it does give you the opportunity, should you choose to keep the conversations short, to potentially avoid the in-depth conversations that could potentially lead to awkward questions.

Prior to these events, my family decided how long we were going to be there, largely because we had a pet whom we obviously couldn’t leave outside for an extended period of time. This allowed me to have shorter conversations with fellow party-goers and learn more about them.

Tip #4: Be Polite and Be Funny

 I’ve found that one of the best and most effective ways to deflect questions is to be polite. This should go without saying, but being kind will get you somewhere. When I have come across awkward questions, I’ve often deflected the question by politely declining to answer before deftly shifting the attention away from myself as deftly as possible. Rather than pushing, I’ve found that if you express your discomfort politely or declining to answer the question, individuals will respect your boundaries and apologize for making you uncomfortable.

Humor also works wonders as well; I’ve found that if you can make someone chuckle or laugh, you are more than halfway there to easing the tension and awkwardness in the room.

The holidays can be stressful enough without the pressure of awkward questions, but as much as we would like to avoid them, they can, and often do, happen. However, it is also possible to answer them graciously and enjoy the holiday season in the process.

[clickToTweet tweet=”How To Answer Awkward Questions During The Holidays” quote=”How To Answer Awkward Questions During The Holidays”]

Have you had any awkward encounters yet this holiday season? How did you maneuver your way out of them?

About the Author

Alisa Tanaka

Alisa Tanaka graduated with a Communications degree from Lewis & Clark College in 2012. She hopes to develop a career that allows her to make a measurable impact on the world while doing something that she loves. Her interests include psychology, linguistics, and mental health. She can also be found reading, watching documentaries, and writing her blog.