Hard Conversations at the Holidays
- Dr. Jennifer Stewart

- Nov 24, 2025
- 2 min read
Large holiday gatherings are ripe for awkward conversations. Whether you are overhearing a racist comment, or being asked personal questions you do not want to talk about, learning how to navigate this with ease will make the holidays less of a headache for you.
Everyone will respond to your reactions differently. Some people, the ones who are more emotionally mature, will be able to take the redirect with grace and apologize. Others will not and may have reactions, and I will talk a bit about how to handle this. For more on this, however, you may want to come back in two weeks for the next post of that covers setting boundaries.
Someone says something racist/sexist/etc.
You can go with a simple “Oof,” some sort of disapproving but non-judgmental reaction that alerts the speaker into realizing they have said something hurtful. For folks who are feeling more empowered, you can use my favorite microaggression intervention, which is where you say, "Oh I'm sorry, I don't understand that joke, can you explain it to me?" This typically leads the person to try and explain the joke, making their bias more explict, to which you can calmly say, "That is racist/sexist/etc" and walk away. For people who are insisting on continuing on with their bias and are trying to argue with you about it, you are allowed to say, "I don't agree and I would like to respectuflly leave this conversation so it doesn't ruin our holiday," and walk away. For the less bold among us, I love a good, "Oh no, my plate is empty, gotta grab another cookie!" and disappear.
Someone asks a personal question you aren’t ready to talk about.
I find this happens most often in families, where people often feel entitlted to information due to being family. You are allowed to answer whatever you'd like and not answer whatever you'd like. For example, if someone asks, "When are you having children?" you can say, "That is a pretty personal question!". It they insist, you can say, "I'm not ready to talk about that just yet." If they continue to push, you can just repeat that, and excuse yourself from the conversation if they continue to insist.
You don’t need to engage in a conversation
If you are not wanting to answer a question, or feel like answering would start an argument you don’t want to start, you are allowed to excuse yourself from the conversation. Joy is part of the holidays, and being able to navigate these challenging questions will allow you to maintain that joy.




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