5 Conversations that Can Hijack the Holidays

Jen Dalton
5 min readDec 6, 2020


This blog includes insights from my latest book Listen: How to Embrace the Difficult Conversations that Life Throws at You. The joy of the holidays is the chance to gather with family and friends to celebrate, virtually or in person. Meals are prepared, festivities planned, and we get to reconnect with loved ones. For many of us, holidays may be the only time of year that we get to see certain family members. While we may love them dearly, there are many reasons you may live far apart — work, past family relationship issues, marriage, divorce, etc. So, on the infrequent occasions that we are together, it may seem like conversations have to happen or they bubble up simply because you are together. If it’s a big one, it can take over the entire Holiday, for good or for bad. When it’s good news, the shift in focus can be a source of joy and additional celebration. But when the topic is tough, it can feel like it hijacked the holiday. Here are five topics that run that risk.

1. Post-election politics.

With the country sharply divided, and a hotly contested election in play, political talk may be inevitable. Worse, we may not even know the final results, and we may be in another contested election scenario, which simply adds an additional layer to a hot topic. Remember, uncertainty is a stressor, and people of all political affiliations will be on edge. Rather than try to cross the political divide and create a convert — or just win the argument — focus on staying positive and supportive. This may mean pressing pause on the conversation, or it may call for working hard to listen rather than react.

Tip: It is okay to listen and simply seek to understand your audience. The goal can be to stay calm and truly listen to someone else’s perspective without judgment.

“The more I asked people about politics and what conversations they had experienced the more people shared how they usually avoid discussing politics with their family like the plague.” — Jen Dalton

2. Aging Parents

In life, we begin being cared for by our parents, but with age, we become the caretakers. Health, mobility, and memory can weaken with age, and it’s reasonable to worry about our parents. Whether it’s a problem that has been developing for a long time or something that has come up suddenly, helping parents to transition from fully independent to some measure of care can be a tough sell to the parents. They may not be ready to recognize their needs, and they may resent the suggestion. A holiday may be an opportunity to observe parents, check to see how they are getting along. If it is time to have a talk, be gentle and respectful of these people who have been adults fending for themselves for a long time.

Tip: If you are going to broach the subject of what is next, consider thinking about what stories people may be telling themselves and how to understand it through questions and listening.

3. Coming Out

For many LGBT individuals, coming out to family is a terrifying but necessary step to take in coming to terms with themselves. If they are living away from family, they may feel, often as a matter of respect, that the conversation is best had in person. The holidays may be the one opportunity to tell your family this important information. For the family of LGBT individuals, this announcement will mean a change. The situation can range from having the well-known but unstated reality finally get voiced aloud to a full shock. Regardless of acceptance, when a person comes out, the dynamic will change, and change can be hard on families. For those with a less than positive reaction, they can channel it into resentment that the focus has been turned away from the holiday. While timing is a personal choice, the holidays may not be an ideal time to do so.

Tip: If you are considering sharing the news with family, consider when to deliver the news and minimize the potential for disruption. Efficient communication is often not effective communication.

4. Marriage

Whether good news or bad, a change in marital status is going to get attention. In some instances, your family might not respond as one would hope — rejecting the fiancé or casting blame for a divorce. Marriage and divorce change the composition of a family, so it is perfectly normal for everyone to have an opinion. Less absolute changes in family dynamics can become apparent when things are not going well for a couple. Holiday stress can add to the tension between a married couple and lead to additional strife. This can play out behind thin walls or in the presence of family, making it an issue for the entire family. It’s hard to look outside of your relationship to consider the impact on those around you, but it’s an important consideration when spending time with family over the holidays.

Tip: When communicating change, it may be that you want to deliver the news when it is convenient for you, but it may not be convenient for your audience. Consider sharing the news outside of the holidays to mitigate memories of the holidays being jaded. If you think delivering the news is a one-way street or a monologue, consider creating space for it to be a dialogue and speaking with people one by one, not in a group setting.

5. Lonely Friends and Family

Every holiday there are people who matter to us who spend it alone. A local friend might not be able to travel to see family, or a family member may not be able to make it home for the holidays. These people can suffer from isolation during a very social time. It’s important to check in on your loved ones and consider scheduling some sort of social, even if it isn’t an invitation to the main meal. Ask yourself who you know that should know each other and consider making an introduction so that there is an additional human connection for the “solos” in your life during the holiday.

Tip: Consider the purpose of a gathering and if it is to connect people who should know each other then how do you create those opportunities? Especially in a virtual way, do you have breakout rooms where people have fun questions to answer to get to know each other? The Art of Gathering is a great book to help people think about the purpose of getting together.

All of these conversations may bring up emotions, particularly due to unknown factors. Give each other space, be more forgiving of yourself and others. Remember the big picture of the relationship — protecting it not losing the relationship because you lose control of your emotions.

Breathe deeply, be present, and listen to help assess what your audience is ready for deeper conversations.




Jen Dalton

Reputation strategist for entrepreneurs & executives. Be a noisebreaker, not a noisemaker. #authentic #gutsy https://lnk.b