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Holiday Conversation Guide: How to Answer the Questions you Hope Nobody Asks

Holiday Conversation Guide: How to Answer the Questions you Hope Nobody Asks
I'm Stephanie May Wilson!

I'm an author and podcaster and my specialty is helping women navigate big decisions, life transitions — creating lives they love.

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When I was single, there was a part of me that dreaded the holidays. I just knew that at some point I’d get the question, “So, are you still single?” 

“Why yes, Aunt Karen. I am still single. Thank you for asking.”

And now that I’m married, it’s still just as bad. 

“When are you guys going to have kids? Why haven’t you had them yet? You know, by the time I was your age, I had three of them!” 

The questions seem innocent enough, and the person really is just trying to make conversation. 

But what they don’t realize is that they just poured a whole container of salt into one of your most wide-open wounds. 

I’ve had to think through these questions (and practice my responses to them!) lots and lots of times and so just in case you’re dreading these moments too, I wanted to share what I’ve come up with.

I have two go-to responses…

If you have a good relationship with the person asking the question, if they're kind and gentle in their tone, and if you can tell they're just trying to connect with you — to hear more about your life, my favorite tactic is to give their questions some direction.

They want to hear about your life, they're just not sure what questions to ask. So I try to help them out!

Here’s what this looks like played out: 

Someone asks:

“So, are you dating anyone?”

(Or, “So, are you guys planning on having kids any time soon?” Or, “When are you two going to get engaged?” or fill in the blank with any other question you are TOTALLY not prepared to answer at Thanksgiving dinner in front of everyone.)

And you respond with: 

“You know, that’s not where my focus is these days. My focus is actually on _______.” And then tell them about your work/studies/friends/upcoming trip.

This is a win for both of you. You don’t end up crying at the dinner table, and your family member gets to hear about your life, which is what they actually wanted in the first place. (They did not go into this conversation hoping to hurt your feelings!).

And really, that’s the thing I’ve come to understand. 

As much as I’ve wanted to burst into tears when someone accidentally steps on one of these emotional landmines in my life, in the past few years my anger in these moments has melted into compassion.

At family functions, we're just trying to make conversation. We're trying to catch up, show interest in each other’s lives, and if we haven't seen each other in awhile, we're not sure what questions to ask! And the thing I've come to realize is that if we don’t know what questions to ask, we certainly don’t know what questions NOT to ask. You know? 

But, that being said, sometimes the question asker isn't quite so gentle.

Sometimes they become pushy, judgmental, give unsolicited advice, or say things that are totally inconsiderate. And when this happens, here's my go-to response, “Thanks so much for your interest, but this is not something I discuss with people outside my inner circle.”

Now here's the truth… I am NOT good at giving this response. I'm much more likely to cry in front of a stranger, or give them every detail of my relationship or medical history than I am to give this response. But it's something I'm working on.

These are tender, important, sacred areas of our lives, and it's not healthy OR helpful to have everyone weighing in and giving us their opinion.

We are allowed to set some boundaries, and that response is the best way I've found in which to do that. (I do tend to follow it up with a sweet, “But tell me what you're up to! I'd love to hear!” so it doesn't feel quite as harsh).

Friends, I know the holidays can be so hard, especially in moments like these. But I hope that having these answers in your back pocket helps. I know it has for me.

Oh, and just one more reminder I think we could all use these days:

You are loved, you are good enough, you are not failing, and you are not falling behind in life.

… and you’re not alone. 🙂 

In your corner always,


P.S. If you could use some help navigating singleness, dating, relationships and more this holiday season, this resource is for you!

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When I was single, there was a part of me that dreaded the holidays. I just knew that at some point I’d get the question, “So, are you still single?”

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  1. Amber says:

    I always got the questions about jobs and work: “so you’ve graduated, what are you going to do now?” And that one question frustrated me more than anything because looking for a job wasn’t enough. One of my friends started saying “I’m packing my bags to go whenever and wherever God calls”. And oh how I love that response! What I’m doing may not seem important to the world, but God has me in a place of growth, preparation, and waiting! He will use this time so that in the next season I can serve even better! It’s okay if you don’t have a job or any idea what you want to do. Serve God in those moments and use this time to grow in love for him and his people. Pack your bags. He will give you more directions eventually!

  2. Andrea says:

    One of my favorite go-to’s for the “are you dating” question is, “Not at the moment. Why? Did you have someone in mind?” Obviously, you have to be game to be set up to use this response because they might! But I’ve found it’s a good response both for people who are sincerely interested and those who just want to gossip. If they’re interested and care, they might set you up with someone great or at least file away that you’re open to being set up if they meet someone who might be a good fit in the future. If they’re just making conversation (or searching for gossip fodder), they’re not likely to ask again because you’ve subtly told them it’s not their business unless they’re willing to actively help! I’ve found that turning the tables away from what you’re doing in your dating life to what they’re doing to help you in your dating life is a pretty effective way of sifting between those who actually care and those who don’t.

  3. […] read a great article the other day by Stephanie May Wilson on how to answer these questions and the one thing that stood […]

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