Thanks, don’t ask.I think you’re right about the confidence thing. But in my experience, if you focus on the little things, you wake up one day with confidence almost without realising how you got there.
Picking up where I left off (dealing with breaking in to groups when you are alone in a crowd) remember to keep moving. There is a natural rhythm to the sort of functions I am talking about - conference dinners, work mixers, weddings of obscure relatives, etc. Early on you are supposed to circulate, in the middle game you are supposed to coagulate, in the end game, you separate.
So, when you are busy peddling the cornchips and pate, if you feel yourself striking something up, remember you are in the circulation phase and not to cling too long, even if things are going well. How long is another of those things you can only know from experience. If you’ve found a point of connection, don’t exhaust it - leave with “unfinished business” so you have a point of connection later. If there is someone you particularly want to come back to, say “I’d better keep moving… catch up with you later, and we can finish this conversation then, OK?” with your most engaging smile. If you cling too long like a drowning man to a lifebuoy, you’ll look desperate. Breaking off gives you time to think about a few things to talk about later, but don’t overthink this. Just a few general topics; nothing too planned.
Remember that those little groups tend to form and reform as people move in and out of them, so you will almost certainly have a chance to revisit a person of interest a bit later on in the coagulation phase as people have sorted themselves out into groups with a little more staying power. Keep a loose eye on the person/s you were interested in talking more to, and take your chance during the inevitable lulls and break-ups in crowd movements associated with that person. If you can get them alone (like when they’re getting a drink) even better. (Do try to be casual about this, though. Pouncing like a seagull on a chip is not a good look.)
Pick up where you left off, or try one of the other openers I mentioned above. If you’re getting a drink, why not ask how good the wine is? Or come up with your own way in to a conversation. It’s all good. Now you can spend a bit more time with one person or a smaller group. The ice has been broken; by this stage you’ll be getting smiles and recognition. Remember that you have to reveal a bit of yourself too, but be humble. Bragging is tacky. Being mildly understated impresses more than being overstated. It’s not given to everyone to be the life of the party, but you can be light-hearted.
By now you’re through to common ground (“You’ve just come back from Vilnius? I love Vilnius/I’ve always wanted to visit Vilnius/I’ve never heard of Vilnius-it sounds so exotic!”). Absolute gold is finding friends in common (“You met the groom working for Sue Grabbit and Run in Boston? My mate Ken used to work there. With the blonde Mullet? That’s him!”). The simple fact that fate has conspired to put you in a room with these people means that you almost certainly will have a number of things in common. Finding the first is the hardest; the rest just happens.
The separation phase is when everyone is deciding where to kick on to after you are finished where you are. Some events come with an expectation you’ll go home, some with an expectation that you’ll go to another venue. With your new friend/s, you’ll probably get yourself involved in one of those group discussions about “Who wants to go to Studio 54?” or wherever; even if you are on the periphery, you’ll get invited along. By now, other people are asking you all the ice-breaking questions because you are legitimately part of the group. And feeling like Elvis with all this attention.
And awa-a-a-a-ay you go.
Remember that these events are not for deep discussions about the meaning of life, personal tragedies, or the excruciating minutiae of your work. This stuff can wait till you know the people you’re talking to better. Upbeat is the spirit of the hour. A little self-deprecation humour is in order - paradoxically, it makes you look more confident. Who else but a confident man could joke ruefully about his fly being undone when he met the President of the company? Making yourself a little bit vulnerable like this is engaging (but like anything, can be overdone).
If talk about travel and cultural ephemera seems low-brow, remember that literally any subject can attract observations at any point along the spectrum of intelligence and insightfulness.
Social conversations of the sort about which we are speaking are a dance - you constantly mutually adjust to your partner’s steps, and you both have fun when your world becomes a little larger for having known something nice about someone else. They are not a fencing competition whose object is to win or lose. They are not applications to the Nobel Committee. They are not opportunities to show off by brain-dumping everything you know about the mechanical innovations of the Wankel Rotary Engine. They are not really about the apparent content of the conversation at all. The apparent content is merely a lens through which you each gain insight into the other’s personality - kindness, generosity of spirit, sense of humour, and so on.
In this conversational dance, just as you asked open ended questions to give the other person a chance to say more than yes or no, so when you are asked questions which give you a chance to reveal something of yourself, your answer returns the favour. You ask a new question at the end, or just expand the topic sufficiently so they have somewhere to take it when you have finished. After a very little while, this becomes instinctive.
Don’t beat yourself up if some conversations just die. Even the best conversationalists can’t make every post a winner. It doesn’t mean they don’t like you, just that you were foxtrotting while they were waltzing and the dance didn’t quite get off the ground. Smile. Move on. “I’m going to get a drink/going to the little Virginian’s room/talk to my supervisor/catch up with some other people” is a common generic exit strategy. Everyone understands and forgives these as courtesies to avoid awkwardness. As you get more adept, you can fashion your own that seem better fitted to the moment and therefore less cliched.
Smile, laugh readily, don’t take yourself too seriously, and believe that other people are genuinely fascinating and that behind the mask of aloofness, they really want to show you that, and want to see the same in you.
Once again, best of luck!