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Three Awkward Thanksgiving Questions— and How to Handle Them

Three Awkward Thanksgiving Questions— and How to Handle Them

Written by Ashleigh Kluck


In my family, Thanksgiving is a holiday that’s much looked forward to every year. My husband and I have family spread out all across Oklahoma and Texas. It’s one of the two times a year when we all get together—which means it’s guaranteed questions about babies, careers and future plans will pop up for us. We’ve had lots of conversations about the future, so we’re prepared for this. Even though we’re prepared, I can relate to the “Um...” and “It’s just not the right time” answers you might give at Thanksgiving dinners. While those questions have great intentions behind them, it can be frustrating when you don’t know how to answer them. Picture your cousin flashing a huge rock on her finger to Aunt Sue, and you’re getting bombarded with questions about your last relationship—the one that ended three months ago. Awkward.

Let’s break down some of the most common Thanksgiving fire-round type questions, and what you can do and say to feel more confident about sharing updates about life.

Question 1: “How are you still single?”

After walking in the door to the sweet smell of pumpkin pie and a round of warm hugs, grandma says, “Oh … you didn’t bring anyone home this year?” You might stare down at your feet, shake your head or immediately try to change the conversation. It’s almost guaranteed someone at the dinner table will be concerned about the fact that you’re single. If you were raised in the South, like I was, you’ll hear the phrase “bless your heart” more than once. The harsh truth is that the older you get, the more this question will be asked.

Your family want to see you happy, loved and appreciated for who you are. Their intentions are good, but it can feel like a ton of bricks crashing down when you walk in alone at Thanksgiving. Whatever your reason for being single—own it as much or as little as you want to. If you’re comfortable sharing that your last relationship was toxic and now you’re focusing on building a business, tell them that. There’s no law that says you have to spill all the dirty details. Share if you want to, and pivot the conversation if you’re feeling uncomfortable. Here’s a few responses to help prepare you for this question, no matter your situation:

“I’m taking some time off from the dating scene, and putting all my energy into making myself happy right now.”

“Since I went through a recent breakup and still healing, I’d prefer not to talk about it right now. Let’s just enjoy our time together today.”

“There’s someone I’ve been seeing. Since it’s new we decided we’d see each other later without the pressure of sharing the holidays. Can you pass the green beans?”

Question 2: “When are you going to have babies?”

The most common question asked at Thanksgiving, ever. Your window is closing, sweetie. Technically, it’s not, Aunt Sue. Even though 30 is creeping up on me, I still have plenty of time to have children. Oh, but what if it’s too late? What if you find out later that you can’t have kids? Well, it’s 2018 and there’s more than one way to become parents.

Here’s the bottom line: It’s up to you and your partner to decide if and when you want to have children. Questions will be asked, and you might feel pressure. While I believe there’s never a perfect time to have kids, there’s nothing wrong with wanting to check a few things off your list before doing so. I want to finish college, and line out my career. You might want to build a house. Whatever your reason(s) for waiting—it’s valid because you say it is. Aunt Sue isn’t raising this future baby, you are. Here are a few different ways to address the question or pivot the conversation:

“We are working on [fill in the blank] right now, and it’s important to us that we get these things done before we have a baby.”

“I know you’re ready to have a grandchild, but we’re enjoying just being married right now. We’ve actually got a few adventures planned this year that we’re really excited about. Didn’t you say you’ve been to Oregon before, Aunt Sue? I’d love to talk to you about where you stayed.”

“We’re trying and haven’t had any luck yet—but we’re hopeful. Even if it doesn’t go as planned, we still have other options. Now tell me, when are you starting your Christmas decorating?”

Question 3: “When are you going to get a real job?”

Most of our parents (and grandparents) grew up in a time when it was important to find a stable, long-term job with benefits. Today, according to a report by FlexJobs, 3.9 million United States employees work from home at least half the time. Online businesses are popping up left and right. Being an Instagram influencer is a legit job title. You don’t have to have a MBA to build a seven-figure business anymore. Even though our parents and grandparents are using the internet a lot more today, they still don’t quite understand how posting travel photos on a social platform can generate a full-time income. This means dinner table conversations can be pretty intense when you tell them you quit your office job to move into freelance photography. When I moved into social marketing, I didn’t want to tell anyone until I landed my first client. You might be inclined to do the same (especially if you’re just starting out)—but don’t. Building a business is a bold move, and if you’ve made the decision to do so, don’t shy away from those conversations. Tell them your plans, and above all, don’t let their fears project onto you.

But, it’s always good to have a plan B. When these questions pop up, here are a few ways to address them without it taking over the entire Thanksgiving dinner conversation:

“I’m really excited about what I’m working on, and I’d love to have your support on this—even if you don’t totally understand right now. I’d be happy to tell you more about it later.”

“I understand you’re concerned, but I’m not afraid. I’ve done the work, and now I’m going to see it through. Even if by chance it doesn’t work out, I’ve got a plan B.”

“I’d be happy to tell you what I’m working on, but let’s do it after dinner. It’s a lot to explain over turkey and dressing.”

I come from a large, beautiful family I wouldn’t trade for anything. Their opinions matter to me. But at the end of the day, I know the choices I make are my own. Regardless of what questions are asked, what statements are made or what fears your family has for you, you’re in charge of the way you want to live. I know that’s equally as scary as it is empowering, so before you step through the door, prepare yourself for these questions that are bound to pop up. Run through the answers in your head so you aren’t stumbling over your words.

And here’s the bottom line: If you want to enjoy single life while you invest in yourself, embrace it. If you want to wait to have babies, wait. If you want to quit your job and start that online store, do it! Be brave. Be proud of where you are in this moment. And be thankful for elastic waistbands.

Happy Thanksgiving!


Ashleigh is currently traveling the U.S. with her husband, Jake, while finishing her B.B.A. at Southeastern Oklahoma State University (cue grad cap toss in May 2019). She’s a content creator, social media manager, and blogger on all things business. When she’s not working, you can find her out exploring new cities with her husband or wandering around the office supply aisles of Target. Connect with her on the ‘gram

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