15 Ways To Start Conversations at Holiday Parties

Holiday parties provide several unique opportunities. In many communities, local nonprofits hold holiday concerts, fundraisers or parties for members. Community leaders and major donors tend to show up. Everyone is in a good mood. However, like a high school dance, it is easy to feel out of place. How can you engage with a total stranger? Let us look at 15 easy ways to get conversations started.

  1. The person standing on the buffet line. You have more time than you might imagine, especially if the buffet line moves slowly. I always mention “I am preparing two plates, so my wife does not need to stand in line. It’s a very efficient way to do it.” They usually agree, realizing if everyone did that, the line would be half as long. This can lead into introducing yourself and asking about their connection to the organization.

  2. The photographer from the local newspaper. If you know them, they have likely taken your picture before. It makes good sense to acknowledge them, because they are often considered invisible by others. “Do you get any time off during the holidays or are you always going from event to event?”

  3. Intermission at the holiday concert. This is usually the time when everyone id at the bar getting drinks or if you were in London, picking up your preordered drinks. In our area, sometimes the community concerts are held in a church. Alcohol is usually prohibited. This leads to my mentioning it’s “The largest gathering of people in Bucks County without alcohol present.” Like the buffet line example, you have time to chat.

  4. The person wearing the red and green outfit. They have put effort into dressing for the holidays. A compliment is always a good idea. If they are wearing a Christmas sweater (assuming it’s not an ugly one) you can compliment them and ask if they have others to wear during the season. In my former office, I worked with another financial advisor who had 24 different Christmas sweaters for the 24 days leading up to Christmas!

  5. The person with the good tan. They have either just gotten back from somewhere sunny or are headed in that direction. This is an opportunity to talk about holiday vacation plans. Regardless if they are headed out, you can also ask about their past travel this year or their travel plans for next year.

  6. The compliment. That is a great pin! It is a beautiful piece of jewelry. (Is it real” would be inappropriate.) “That’s a great watch!” is good too. I like the expression “Is it a family piece” because it can get them talking about the origin of the item. If it is a family piece, there is a story there. They might be collectors. Regarding watches, they can be a source of pride. I have heard watches described “on a square inch basis, it’s the most expensive item in the world you can buy.” Here is a reference for one valued at $55 million and another at $ 31 million. (1)

  7. You are in line at the bar. Similar to the buffet line, you might be in for a wait. It’s another opportunity to ask: “can you see what kind of scotch they are pouring?” Some events only feature wine, beet and water. You can ask a similar question about the wine.

  8. The harried looking person. They might have too many things to get done and not enough time to fit it all in. It is a safe assumption everyone does shopping in December. “Have you gotten your holiday shopping done?” When they answer, you can talk about your shopping adventures.

  9. The host at the party you are attending. You should thank them for inviting you to their home. You should also make it a point to circle back before you leave and thank them for a wonderful party. If the host is a client, you are probably surrounded by their friends and acquaintances. I like an expression I learned from a local financial advisor: After thanking them, you ask: “Is there anyone here you think I should meet?” They should immediately think of someone, walk you over and introduce you.

  10. Parents of children from the same school as yours. Everyone knows when the term ends and the new one starts. You might talk about vacation plans. Are they going away for the holidays? They might have a skiing vacation planned.

  11. Parents of children from a different school. This could be a conversation about vacation plans too. Now the timing might be different, so you can inquire when the last termed ended and the new one begins. Do they have any plans? Is a holiday cruise on their agenda?

  12. The local accountant. You might recognize them. If not, this comes out during the “What do you do” icebreaker conversation. Is this a busy time of year for them? You might add it is busy for you, because clients need to do year end tax loss selling. Older clients need to get those Required Minimum Distributions (RMDs done). They should respect you because you know this is important and put your client’s interests first.

  13. The major donor to local charities. If you are involved on the nonprofit circuit, you know who these people are by sight. They either support all the major causes or they have one favorite and are their major donor. They often serve on the board. Saying nice things about the good work the organization does is a good conversation starter. If you attended their major fundraising event earlier in the year, you might mention that too. You supported their cause.

  14. Someone you promised to have lunch with multiple times. We have all done it. You have said: “we must have lunch together.” You never followed up. Apologizing can be awkward. A better strategy is to pull out you calendar or phone and say: “Lets set a date now.”

  15. The person who sent you that great Christmas card. Plenty of people still send out cards. Some can be quite ornate. Ours have been drawn by the same artist since 1983, which means he has been creating a new card for us over forty years! Mention “I got you card!” If they enclose a holiday letter summarizing the year’s activities, mention it. Cards often feature family photos. You might mention that too. This shows you have a good memory and remember details.

Starting conversations with strangers can be incredibly easy. Be open. Smile. Let them do the talking. Listen and ask questions based on what they told you. Now you’ve got it.


Related: Why Everyone Needs a Good Accountant