Social Briefings are short bi-monthly dispatches that offer practical tips to improve your social skills. Read more on their raison d’etre.

In the first four social briefings, we laid down some mindset fundamentals that undergird and enhance all other social behaviors and habits.

Now we’ll start delving into the nuts and bolts of social effectiveness, and we’ll begin with that most dreaded of situations: attending an event where you know no one, or close to no one.

Maybe you’re attending a party where you only know the host (a good host will introduce you around and even start a conversation between you and someone you’re likely to get on well with, but that certainly doesn’t always happen). Or perhaps you go to a shindig with a friend, but he disappears into the crowd as soon as you get there, leaving you standing by yourself. Perhaps you’re attending a networking event, where the whole point is for a bunch of strangers to get to know each other…but that doesn’t make doing so any easier.

Any way you slice it, going to an event where you don’t know anyone is an anxiety-inducing affair. You stand there awkwardly, unsure of how or who to start talking to, and feeling like you stick out like a sore thumb.

So let’s tackle some practical strategies gleaned from Jeanne Martinet’s The Art of Mingling for making this scenario go a little smoother.

How to Enter the Event Itself

Fake it ’til you make it. Even though you probably feel quite tense and nervous, try to act the opposite. When you exude comfort and confidence, you’ll seem more warm, friendly, and approachable, and you’ll act less awkwardly. As Martinet says, “For the first few minutes of a difficult mingling experience, what you project is more important than what you may be feeling.” Projecting ease amidst knocking knees isn’t easy, obviously, but just tell yourself that you only need to gin up some confidence for ten minutes; by that time, the ice will hopefully be broken, and you’ll be on your way to actually feeling comfortable.

Talk with some fellow “outsiders” first. The easiest people to start talking to at a party are those who feel as lost as you do. You can find them by looking for folks who are dressed a little inappropriately for the event, standing tentatively by themselves or in a pair, wandering around aimlessly looking at the pictures on the wall, or just staring blankly around the room like you are. They’ll likely welcome your advances, and feel as relieved as you will to be talking to someone else.

This is a great way to get your social skills “warmed up” for the event. If it turns out you and this other “outsider” hit it off, feel free to talk for a while. But if you’re at the event to meet more than one person, and/or you’re not connecting with this individual, then after a few minutes it will be time to try your hand at initiating a more challenging interaction: entering a group of people already having a conversation. (Here’s how to deftly exit your current conversation.)

Look for people you think you might connect with. When you enter a party, most people will already be talking to each other in little groups. Your task will be to decide which group to try to enter and introduce yourself to. You obviously want to find people who look friendly and receptive. But you should also scan for guests who seem like “your kind of people.” Folks not only wear their personalities on their faces, but the way they dress and hold themselves also tells you a lot about them.

You typically instinctually know if someone is the type of person you’d potentially get along with, and it’s easier to try chatting up someone (or a group of someones) with whom you likely share interests, than those with whom you have little in common.

Look for an “open” vs. “closed” group of people. When people are standing close together, leaning in to each other, and engrossed in a conversation, consider that group to be wearing a “closed” sign. Such a circle will not only be physically hard to enter because of the lack of space between participants, but your entrance will likely disrupt the conversation going on, leading to an awkward silence, and even a bit of resentment from those who don’t appreciate your interrupting their good time.

Rather than taking on the challenging endeavor of entering a “closed” group, look for an “open” one instead. Here the participants are gathered more loosely, the talk seems more light, and the participants may already be looking around the room for other conversation opportunities. It will be easier to add yourself to the mix of this more open circle without creating a significant disruption.

Pick a large vs. small group of people. Small groups of two or three people are the hardest kind to enter. Your entrance is more conspicuous, and your chances of creating an unwanted and awkward interruption is high.

Entering a larger circle of people is easier, for the simple reason that it’s less conspicuous and gives you more options. Even though your entrance will be less obvious, there’s likely to be at least one person who will notice you, and initiate conversation. Or, if nobody notices you sidle up, then that’s good too; you’ll get a chance to catch up on what’s being talked about and wait for an opportunity to add something to the conversation or offer an opening line or introduction. And, should you tune into the discussion, and decide these folks aren’t your type, it’s easier to slip away as inconspicuously as you came.

4 Ways to Enter a Group of People

Once you’ve picked a group of people to try to join, how do you then initiate contact and start chatting them up? Here are a few strategies for your opener:

Offer a compliment. An easy way to move into a circle of people is to offer a compliment to the group as a whole (“You guys seem to be having the best time here”), or to an individual in the group. If doing the latter, try to offer a compliment that the rest of the participants can chime in on. Whenever you’re entering a group, you never want to segment it by drawing one person away from the others; that can break the web of energy that participants have been weaving, and he or she may resent you stealing their attention away and cutting them off from the existing conversation. Compliments like, “I heard you brought the stuffed mushrooms and wanted to say how amazing they are,” or “I just wanted to say you have the best beard in the room,” work as praise for the individual in question, and are also easy for the rest of the group to riff on: “Those mushrooms were awesome,” “That beard is something to behold.”

Ask a question. This is another easy opener, and again, aim to ask questions that involve the whole group rather than just one person. “Do you all know who brought the stuffed mushrooms?” “Do you guys know if that’s Jason’s son? He’s gotten so big since I last saw him, I hardly recognize him!” “What’s the best thing to eat after a tough [fitness] class like this?” Asking an opinion is always a good way to kick off some group discussion: “What color do you think this tie is? Red or orange? I think red, but my wife and I had a ten-minute debate about it before I headed over here.”

Drop-in as a “passerby.” Stand as casually and inconspicuously as possible right outside a circle of people, trying not to be noticed. Listen in on what they’re talking about for a bit, and then offer your own comment at an appropriate moment. Don’t be hesitant and apologetic: “Were you all talking about X? Mind if I, um, add something here?” That makes you seem like a creepy eavesdropper/interloper. Rather, act as though you just heard someone’s comment in passing by and wanted to put in your two cents. Be direct and start talking with the group as if you’d already been in the circle awhile, acting as if it’s perfectly normal for you to be there. Confidence is key here.

Take the honest approach. Sometimes being incredibly straightforward is the most winning tack to take. “Excuse me, I hope you don’t mind my coming up to you out of the blue like this, but I don’t know a single person here. I’m Rob Smith.” It’s not threatening, people readily identify with being in your position, and, often endeared by the fact you’ve deprecatingly put yourself in their hands, they’ll typically be willing help you out and include you in the conversation.

When it comes to choosing which strategy to employ, pick the one that meshes the best with your personality and the occasion, and will thus come off most naturally.

Of course, in an ideal world, before you even have to approach other people, someone else will have already approached you. There are ways to increase the chances of this happening, and that’s what we’ll talk about next time.

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