How to Answer Uncomfortable Questions This Holiday Season, According to a Psychologist

Dr Jessica Yu

Written by Jessica Yu, Ph.D.

Published 12/21/2023

’Tis the season for celebration, joy, family gatherings and uncomfortable questions. 

As much as I love spending time with my family during the holidays, I also dread the awkward questions and conversations that are sure to come up. When I was in my early 20s, my very loving and well-intentioned aunts and uncles hounded me with, “Do you have a boyfriend?”

When I finally introduced them to my then-boyfriend (now husband), they asked, “When are you getting married?” After we got married, they wondered, “When are you having kids?” And ever since having my first child, the question has morphed into, “(When) are you having more kids?”

I know I’m not the only one who faces the uncomfortable-questions-during-the-holidays challenge. My therapy practice typically becomes busier this time of year, as patients request additional sessions with one question in mind: How do I navigate uncomfortable questions from my family this year?

Below are some tips to help you prepare for the awkwardness, as well as suggested responses to some common questions.

1. Be wary of jumping to conclusions or taking things too personally.

I find that when people receive uncomfortable questions, they automatically assume that the questions come from a place of judgment. They believe they’re being asked about their relationship status because others believe they’re not working hard enough at dating. Or they’re being asked whether or not they’ve gained weight because they look fat. 

People ask questions for lots of reasons. Sometimes they’re genuinely curious. Sometimes they just want to fill the silence. It can be helpful to hear family members’ questions for what they are, without trying to assume any particular intent.

2. Remember that you can say as much or as little as you wish.

When someone poses a question you feel uncomfortable answering, you may feel like you’re in the hot seat. But you actually have the upper hand. You get to decide whether and how you want to respond. 

For example, if someone asks you about your relationship status and you’d rather not get into it, you can tell them, “I’m single at the moment,” and leave it at that. If they press for further details, you can be a broken record and say, “I’m single right now. There isn’t much more to say.” And then you can gently steer them towards topics that you may be more interested in, or excuse yourself to move onto another activity.

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3. Find a friend.

If you look open for conversation, you’re more likely to be a target for uncomfortable questions. Look for a trusted family member or friend during your holiday gathering, and use them as needed. This may mean sticking close to them so that you appear otherwise occupied during the party, or using them as an excuse if things get too awkward for you.

4. Take a break if you need one.

If uncomfortable questioning at your holiday gathering gets too overwhelming, take a break and do some self-soothing. Go to the bathroom, take some deep breaths, and splash some water on your face. Find a quiet room, turn on some music, and enjoy the solitude. Even better, take a walk outside, get some fresh air, and get those endorphins flowing.

Question: Why are you still single?

Potential Response: “I simply haven’t found the right match for me yet.” This answer is short and underscores that you are the authority in your relationship world.

Question: When are you getting married?

Potential Response: “We’re enjoying our time together. We’ll get married when we want to get married.” This answer works for almost all variations of the dreaded “When are you getting married?” It works for people in new relationships just getting to know each other, those in longer relationships who may be feeling pressure to say “I do” and those who are engaged but haven’t yet set a date.

Question: When are you having kids?

Potential Response: “I appreciate the question. I don’t have an answer.” This answer works for all sorts of scenarios – whether you’re interested in having kids or not, whether you’re trying to conceive or not, and more. It also underscores a major truth – which is that you can’t really schedule having a child.

Question: Have you found a (new) job yet?

Potential Response: “I’m still working on my next move.” This answer is intentionally vague and likely truthful. It indicates that you’re working on something, whether that be revising your resume, answering calls from recruiters, rethinking your career or taking a pause from your job hunt to attend to other aspects of your life.

Question: Have you lost (or gained) weight?

Potential Response: “Let’s talk about something more interesting.” Given that this question can open up a whole can of worms related to your appearance, appetite, eating habits and more, it might be worth forcing a change of subject. Ask the person what TV series they’re currently watching, what present they’re hoping is awaiting them or even their thoughts about the weather. This approach also works well for other tough subjects you’d like to avoid, including politics, for example.

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Question: Are you still depressed?

Potential Response: “Thanks for thinking about me. I appreciate it. Like everyone, I’m a work in progress.” This answer indicates that you appreciate the asker’s concern, but doesn’t dive into the intimate details about your current emotional state. And it underscores yet another major truth—that we are constantly evolving and working on ourselves.

In addition to the above tips and suggestions, remember to be mindful! Enjoy as much as you can of your family’s holiday gathering, and realize the less comfortable moments will soon pass. Happy holidays!

This article is for informational purposes only and does not constitute medical advice. The information contained herein is not a substitute for and should never be relied upon for professional medical advice. Always talk to your doctor about the risks and benefits of any treatment. Learn more about our editorial standards here.

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