8 Cringeworthy Questions You'll Face This Holiday Season—and How to Respond


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Ahh the holidays. It's so easy to love this season, but it's also easy to hate it. Why does this time of year bring on so much stress when it's supposed to be all about cheer? For me (and maybe for you too), a couple of things come to mind: end-of-year work projects piling up; invitations and obligations to festive gatherings (while fun, they can also be a lot for our inner introverts); financial worries (how much does a plane ticket home cost?! The pressure to buy something for everyone on your list); and lots of family time.

The last one shouldn't seem stressful, but a lot of us know how tricky family dynamics can be. (If this doesn't apply to you, I need to ask you a million questions). Whether you have a big family, or a small one, dealing with them this time of year can be heartwarming, nerve-wracking, happy, annoying, funny, and sad all at once. Sure, reuniting with loved ones is so special and fun, but old issues and differences can really lead to some awkward and tense moments.


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So how can you get through this time of year and still keep your familial relationships intact (with minimal or zero fights)? Or at least avoid anything that disrupts you and others from enjoying the season? We asked Madeleine DiLeonardo, MEd, LPC, NCC, a licensed professional counselor and founder of Mind Body and Soul by DiLeonardo Wellness, and Myka Meier, founder and director of Beaumont Etiquette and the Plaza Hotel's Finishing Program, and author of the upcoming book, Modern Etiquette Made Easy for their advice.

For starters, when you're filling out your social calendar for the season, it helps to make some time for yourself and things that make you feel good. "Book-end stressful family gatherings with things that feel good for you," DiLeonardo suggests. "If you suspect that a situation or event may be difficult, be sure to create time for yourself to do something you enjoy before or after. This creates the capacity to handle more challenging situations, whereas if you go into the holidays feeling stressed or anxious, difficult dynamics may feel harder to handle." Some things you can do are head to your favorite coffee shop to get some space if you feel you're being surrounded by people at home or make plans to see an old friend after a gathering.

When it comes to the holiday gathering itself, DiLeonardo says it's important to focus on being present to the smaller things that feel positive or neutral. "For example, spending more time talking to a cousin that you get along well with or focusing on eating a tasty meal," she explains. "If during or after the gathering you are feeling more vulnerable or self-conscious, be sure to process these feelings but not dwell on them. We can often be really hard on ourselves, and if we are feeling exposed or emotionally drained around family, this feeling becomes more intense." Know that your feelings are valid, but focus your energy on things that make you feel good.

And when the conversation turns awkward or tense—whether it's at the dinner table or just small talk—it's okay take control of it, but do it with respect. "It's important to respect those around you so if you're uncomfortable with a situation you can politely excuse yourself from the situation," Meier says. "You do not want to embarrass or shame someone, but in the worst case, you can pull the person aside or quietly tell them that this is neither the time nor place for whatever is happening (conversation, debate, etc.) that is causing awkwardness."

If you find that you need to remove yourself or someone else from the conversation to avoid a heated argument or debate, Meier suggests asking to help in the kitchen or set the table. You can also go outside for some fresh air or a different room for some quiet time.


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Remember to keep your cool and stay composed—this can be achieved by taking your time rather than getting caught up in the moment. "Think before you speak and take deep breaths to calm yourself (it's scientifically proven that oxygen to the brain calms!) before saying anything you may regret," Meier says. "Think about how you want to phrase what you want to say, and then calmly in a soft or normal voice ask the person or group to change the topic. If you can predict there may be an awkward family conversation or question, think about your reply ahead of time so you are not caught off-guard."

DiLeonardo agrees with the latter advice because it can help minimize the anxiety or background noise as you prepare for the event. And to switch the focus off of you, she suggests asking several questions of your own and allowing the other person to share something about themselves.

The good news about this idea is that it can be thought about beforehand—it's pretty easy to predict the common conversation topics or questions that might be brought up at a holiday gathering. To prepare you, we compiled a list and asked DiLeonardo and Meier for some response ideas:


1. Are you STILL single?
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Samantha Estrada/Stocksy)

If a woman had a nickel for every time she was asked this at a family gathering, I think it might close the pay gap. Too facetious? Yes, but this question gets me really riled up as someone who is perpetually single, but guess what, totally okay with it.

Both DiLeonardo and Meier find that there are two ways to respond to this one, depending on the audience and your own preference:

Humorous take

DiLeonardo: "Most of my dates are with the couch,but I'll be sure to let you know if that changes!"

Meier: "I have met some really interesting people, but I haven’t made anyone an offer to stay in my life yet."

Firmer take

DiLeonardo: "Not now, but I'm very happy to be focused on ____ (whatever you are working on at work, school, passion project, etc)."

Meier: "I have not met the right person yet. There are lots of people out there, and I'm looking forward to meeting new people. I will let you know if there is anyone worth chatting about."


2. When are you getting married?
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This question can be uncomfortable, especially if your significant other is with you. You might not know what to say because you haven't talked about it, or you have but aren't ready for the next step yet, or maybe you've only just been dating for a couple of months, or you don't have plans to get married, or you simply might not want to talk about the topic at all. Whatever the situation is, it can be weird.

DiLeonardo: "For questions about getting married or having children, if you do not have or do not want to share a definitive answer, you can respond by saying something like, 'That's something my partner and I are thinking about together and we'll share when we're ready.'"

Meier: "We're happy as we are and not looking to get married right now."


3. When's the wedding?
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Like the one above, there are a lot of scenarios here. You might be engaged but haven't set a concrete date yet, or aren't planning the wedding anytime soon. You could be eloping. You might not be planning to invite the person who's asking you this question. The list goes on and on.

Meier: "We're still researching our options. But we'll let you know as soon as we pick a date!" (Of course, if you're not planning on inviting the person who asked you, we'd leave the second sentence out of this one.)


4. When are you having kids?
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The question can be problematic on so many levels. "This is a tricky one because a couple may have decided not to have kids, or may be going through fertility issues," Meier says. "It's up to the person answering, or couple, to decide how open they want to be with responding." Here's one response idea, depending on your situation:

Meier: "We're enjoying our time together and will let you know when we have news to share."

If you want to avoid the topic altogether for whatever reason, you can also politely and firmly say that you'd rather not talk about it right now.


5. When are you having another kid?
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This one's another sensitive topic. Meier says again, it's up to the couple or person to determine how honest or open they want to be. She gave this response idea:

Meier: "You know we are enjoying our time with ____ (your child's name) so much that we haven't decided when or if we want to have another baby."


6. Comments on your appearance
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You might get some comments like "You lost weight, you look good!" or "You look tired." Sometimes they're easier to take, and other times, they might make you feel bad or self-conscious.

Meier: "These comments are most often meant in a complimentary ('You look good') or concerned way ('You look tired'), and the person saying them may not realize that they're being rude or insulting. If you can ignore them, then do so. If it's a compliment, simply say thank you and move on to another topic. It's up to you if you want to elaborate on why you may look tired (aka, the baby is teething and you've been up all night, or you've been working on a deadline at work)."


7. Any Conversation About Politics
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First you have to deal with family drama, and then you have to deal with your feelings about the political state of the country? Can't we all just enjoy our turkey/ham/holiday dish in peace?

Meier: "In general, it's not a good idea to bring up politics, especially if you aren't 100% sure that the person has a similar opinion as you do on the topic. As the party's host, you can end the conversation by reminding guests that the party is a politics-free zone.

DiLeonardo: "If it's something that you don't want to talk about, simply stating that you respectfully disagree with someone's views but do not want to waste quality time arguing is helpful. If you do want to discuss differing opinions, try to model doing so in a respectful way while also expressing that you remain passionate about your own views."


8. Comparisons between family members
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You might have some sibling rivalry, or find yourself always being compared to your cousin. Whatever the case, it's not fun for your self-esteem when you have someone reminding you that your cousin got a raise or promotion, or that your sibling bought a house, and then to be asked what you're doing with YOUR life.

DiLeonardo: "It's helpful to remember that what is most important is that you are building and living a life that feels good for you. Sometimes, we see family members or friends around the holidays that are not a large part of our lives and yet their criticism still greatly impacts us. Rather than giving power to the things or people that cause us to feel negative, how can you reclaim that and instead focus your energy on the things that you are proud of in your life or the things that do make you feel positive?"

Meier: "You never want to come across jealous or unhappy for someone else's news. Offer a compliment on the good news and if someone asks what is going on in your life (with a comparing tone), you can chime in with happenings and updates in your life if you wish, and then add something you want to talk about to change the direction of the conversation to something you like talking about (like travel). For example, 'That's wonderful news, congratulations! I'm busy with work and looking forward to traveling to Australia in spring. I’m going with a hiking group to see the…'"

Next up: Why Do I Feel So Bummed Around the Holidays? A Psychologist Explains


This article is provided for informational purposes only and is not intended to be used in the place of advice of your physician or other medical professionals. You should always consult with your doctor or healthcare provider first with any health-related questions.

Managing Editor

Sarah is lifestyle writer and editor with over 10 years of experience covering health and wellness, interior design, food, beauty, and tech. Born and raised in Los Angeles, she attended New York University and lived in New York for 12 years before returning to L.A. in 2019. In addition to her work on THE/THIRTY and Who What Wear, she held editor roles at Apartment Therapy, Real Simple, House Beautiful, Elle Decor, and The Bump (sister site of The Knot). She has a passion for health and wellness, but she especially loves writing about mental health. Her self-care routine consists of five things: a good workout, “me” time on the regular, an intriguing book/podcast/playlist to unwind after a long day, naps, and decorating her home.