Can we loop you in? Your next round of holiday cocktail parties will be less awkward with these strategies for asserting—and inserting—yourself.

By Liz Loerke
Updated November 21, 2016
Benn Wiseman
Benn Wiseman

Ask Open-Ended Questions.

A lot of people make the mistake of thinking they have to tell a funny story or make a pithy comment on current events, and that’s not true. You just need to ask an open-ended question. A good question, along with eye contact and a smile, conveys “I’m friendly, I’m approachable, and I’m interested in learning about you.” I work with clients who suffer from anxiety, and I tell them to write a few questions either in a note on their phone or on an index card. I particularly like TableTopics, which are these small cards with conversation starters that you can get on Amazon. They give you interesting questions that everybody loves to think about. Something like “If you had a million dollars to give away, what would you do with it?” That’s great because there isn’t a right or wrong answer, so people will freely share their opinions. Even better, once you ask the question, you don’t have to say anything at all!
—Karen Cassiday, Ph.D., is the president of the Anxiety and Depression Association of America. She owns the Anxiety Treatment Center of Greater Chicago, in Deerfield, Illinois, where she resides.

Get in Sync.

Entering a group conversation is almost like a dance. When you see a gathering you want to chat with, you need to make them aware of your presence. Sidle up to the group, listen in on the conversation, and use your body language to gain entry. Mirror the group. That means if they react to a story, you react. If they laugh, you laugh—but not too loud, because that can be off-putting. The group will instinctively open up toward you to acknowledge that you are part of the conversation. They may not welcome you verbally, but once they physically turn to you, even if it’s ever so slightly, then you know you’re in.
—Elaine Swann is a lifestyle and etiquette expert based in San Diego.

Offer a Round of Drinks.

An easy way to join a group is to pop in on your way to the bar. Interrupt quickly but politely and say, “I’m heading to the bar to grab a glass of wine. Anyone want one?” When you come back, let the conversation continue. You don’t want to be the person who walks in and takes over. I like a “break and exit” approach. When you see that there is an opening in the conversation, briefly introduce yourself: “I’m Glenn. I’m a friend of the family. I just wanted to say hello. Please go ahead—I don’t want to interrupt the conversation.” Then take a step back and listen.
—Glenn Selig is a public-relations expert and the founder of the Publicity Agency, in Tampa, Florida.

Join With a Purpose.

I don’t like to address the group as a whole. I prefer to go in at an angle and talk to one person. I find the easiest way to do that is to give yourself a social purpose. By that I mean, ask for information. Think of it this way: If you were lost in the woods with a dead GPS, would you have a problem talking to people and asking directions? No, of course not. So ask for information, like “Where did you find a parking spot? Do you know if there is an after-party?” Really, any who, what, where, when, or why question will do. If you have a reason to talk to someone other than just making conversation, it’s much less daunting.
—Patrick King is the best-selling author of Conversation Tactics and People Tactics. He lives in San Francisco, where he works as a social-skills and conversation coach.

Compliment Someone’s Shoes.

While it may not be the most sophisticated entrée, it works. If you’re at a holiday party, people have probably dressed up. They’ve made a decision about what they’re wearing, and they hope someone notices it. So if they’re wearing a beautiful pair of shoes or a great pair of glasses, let them know you think they’re fantastic! It’s the shorthand way of saying, “I think you’re interesting.” If you would prefer not to comment on someone’s outfit, compliment the host’s decor or the food. Ideally everyone at the party is there because they like this person. By entering a group saying something positive, you will give off a good first impression.
—Kat Kinsman is the senior food and drinks editor of Extra Crispy (owned by Time Inc., Real Simple‘s parent company) and the author of Hi, Anxiety: Life With a Bad Case of Nerves. She lives in Brooklyn.