I still classify myself as somewhat shy in my travels. There is none of that "charisma" that some people naturally possess when they enter a room; no force of gravity that breaks up a group & draws them to that person.
Still, it must be pointed out that progress has been made through the years, due to a maturing manner, as well as the simple thought that being, or just feeling, alone can be a killer to the psyche.
I credit my first girlfriend (1992-96) for that, though it was a trite forced. As much as I didn't initially talk freely before then, she didn't talk at all. Silence can be as horrible as being alone, so I had to force myself to come up with topics and discuss them. It was amazing how that extra effort continues to pay off up to today.
Especially in a bowling environment, free talk comes so naturally, I wonder why it can't apply to me in other situations. You place me in a bowling center with groups around me, and within minutes we're gabbing like old friends. I bowled on Sunday on the spur of the moment, and within five minutes we were discussing bowling heroes of the past, lane conditions, and were teasing the group to our far right, who were so snockered with booze they were escorted out of the center before their first game ended.
So when a friend confided last night that they can't handle themselves in social situations, to the point of being a hermit, I had to provide advice.
First: Don't feel pressure to go to an environment you think these people might enjoy. You're better off being in a place which makes you comfortable. If I was at a hockey arena, I'd be clamoring for the exits, because hockey is not in my blood. There's no chance of me sharing that love with anybody else, so it shuts down most all possibilities of communication. At your place. you're free to scope around and pick a group you may enjoy.
Second: Screen the group from a distance. No one can accuse you of staring or stalking if you just observe without becoming obvious. A person loaded with booze will not let their natural personality shine through due to being impaired. They take things to such an exaggerated level that you'll forget what you are there for. Human beings are preferred to monsters almost every time. At the same time, watch your obnoxiousness level, too.
Third: Start by commenting on the things they're doing. You will be surprised how the majority of people open up just with a compliment hurled their way. I commented appropriately on the adjoining party's first-frame strike, and the conversation immediately started from there.
Fourth: If you do something out of the ordinary (like hit a cue ball off the pool table or land a wayward dart nowhere near the board), laugh about it, rather than cringe. People around you may laugh about your ineptitiude. If you show you can take it as well, chances are they won't avoid you like the plague.
Fifth, and most important: Don't plot or expect things to happen. Don't come in armed with a script, saying "Today's the day I'll meet fifty people!" Go with just the thought of having fun in mind, and that the friendships are a bonus. You'd be surprised to notice just what comes naturally out of those situations.
Nothing is impossible if given the chance, and that's what I told the friend. All it comes down to is a good eye, good conduct, natural attitude, and a willingness to have a free personality.
