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Thoughtful Conversation Topics for the Holidays (and a Few to Avoid)

Friends Celebrating Christmas

One of the best things about the holiday season is getting together with people you haven’t seen in a while. This time of year often brings the opportunity to catch up with friends and family members. While this is wonderful, it can also be difficult to know what to talk about, how to start a conversation, and how to get to know new people.

Here are some conversation topics and questions that can help you to reconnect, and learn new things about the people you interact with:

  • Conversation Topic #1: Ask them about the most fun or exciting thing they did this year. 
  • Conversation Topic #2: Ask them if anything changed in their life over the last year.
  • Conversation Topic #3: Ask them if they are expecting any changes in the coming year.
  • Conversation Topic #4: Ask them what a typical weekday looks like for them.
  • Conversation Topic #5: Ask them what their favorite ways to unwind are.
  • Conversation Topic #6: Ask them if they like the city they live in (and what they like about it, or what they do there).
  • Conversation Topic #7: Ask them what they are most looking forward to about the holiday season.
  • Conversation Topic #8: Ask them what shows/movies they have been watching (or podcasts, or music).
  • Conversation Topic #9: Ask them what their favorite restaurant is, and when they like to go there (or what they usually order).
  • Conversation Topic #10: Tell them about a favorite memory you have of them.

All of the above topics can help you to learn more about the person, and reconnect. They also open the door for the person to disclose personal information to you if they want to, while leaving them space to talk about lighter things if they do not want to talk about more personal things. However, some questions (which are very common in friend/family gatherings) are inherently personal, and put people on the spot to divulge very personal things.

Woman Stressed Out

Here are some conversation topics that might be uncomfortable or hard for the other person to answer, and that you should consider avoiding:

Uncomfortable Topic #1: Are you dating anyone?

            If they aren’t, or they wish they were, or they just went through a break-up, this is a difficult and potentially painful question. Even if they are, they might not want to talk about it with you. Relationships are important, and it’s understandable to want to know about them. But if you try the other conversation topics from above, and they choose not to tell you about that part of their lives, it’s probably better not to ask.

Uncomfortable Topic #2: When are you getting married?/Aren’t you going to get married?/Why aren’t you married yet?

            Relationships are complicated. They are also very personal, and often very private. If people want to get married, they will, and if they want to announce it, they will. If they don’t want to get married (yet, or ever), they probably have reasons, and those probably aren’t reasons they want to be asked about. Even if you are close with someone, be very thoughtful before asking about this. It’s okay to be curious, but it may not be kind to put them in a position of feeling that they have to explain themselves or divulge very personal information.

Uncomfortable Topic #3: When are you going to have kids?/Don’t you want kids?/Why don’t you have kids yet?

            Again, this is a deeply personal topic. Having children is serious; it is a big decision, and there are a lot of factors that go into it. Having children is an emotional, financial, physical, and lifelong commitment. People have a lot of reasons for why they wait, or why they may choose not to have children. Furthermore, not everyone is easily able to have children. Remember that the person you are speaking to may be struggling with infertility, or may have experienced a miscarriage, both of which are things they likely do not want to discuss. Lastly, they might be planning on having children and feeling fine about it, but that doesn’t necessarily mean that they want to talk to you about it.

Be thoughtful, and be empathetic. Often, we ask questions because we are invested in others’ lives, and want to know more about them. However, it’s good to remember that just because we are curious, and just because we care, does not mean that we are entitled to personal and private information about others. Stick with questions and topics that give them an option about how much to share with you, while also opening new and interesting conversation.

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