Back to "friendly" socializing: In general, I kinda suck at saying stuff I know isn't true, and going for someone's masculinity or for other sources of their self-esteem is something that really doesn't come naturally to me. Back in the old nerdy days I used to clam up in indignation (or sheepish shocked sadness depending on how much I knew the person appreciated me: I mean, someone who's a true friend, and is loyal, and helpful, and nice, and suddenly out of the blue and for no reason at all Attacks Your Weak Point For Massive Damage). Nowadays I just use a wary "are you fucking kidding me" face and, if the other person keeps it up, some dry, deadpan put down heavily inspired in Batman and Quirrelmort (I only wish I could emulate the level of threat post-Azkaban Quirrelmort exuded). (Yes, much of my social repertoire is taken directly from fictional characters.)
I recognize these behaviors as things that I did in such situations when I was younger. Here's what helped me get over that: I realized that, for the most part, people can only embarrass you if you agree to be embarrassed. It's much easier for me to interact in a teasing environment now that I've simply stopped taking it so seriously.
The underlying principle is that everyone has embarrassing stories and characteristics. Participating in making fun of these things, both yours and others', is a way to signal trust and belonging to the other people in the group. The point of this kind of interaction isn't to be cruel or mean; it's that not being able to talk about sensitive topics makes you seem like a member of the out-group. Members of the in-group will generally be less offended by a teasing remark made by one of their own than by the same remark made by someone outside of the group, so matching those differing levels of offense demonstrates your familiarity with the in-group.
Obviously, not becoming embarrassed or offended is easier said than done. I recommend trying not to display or act on the feeling even if you have it. As I worked on doing this, the feeling itself became much less prevalent.
Also, it's important to keep track of which topics are off-limits even for the in-group. People may have issues that are simply too sensitive for the usual teasing, and failing to realize that is another signal of lack of familiarity with the group members, and therefore out-group status.
Followup to Recovering Insufferable Genius
So, we've been talking a mighty amount on avoiding and understanding the common pitfalls and mistakes that plague most human minds for various biological, evolutionary and social reasons. This knowledge is supposed to be used for the sake of learning how to think proprely and clearly about the world, and for the sake of making the right choices, and making them quickly. Both blades of the weapon can have a dramatic effect on how we interact with people. Behaviors that would appear absurd and annoying to us would suddenly gain a history, reasons for their existence until now and even for their continued existence. The incomprehensible people around us suddenly become fairly simple and predictable, to the point that you might, every now and then, understand them better than they do themselves. They also become all that much more interesting. You find yourself observing them, gently pushing their buttons as you eagerly wait for what they are going to do next. Of course, this applies just as much to you yourself. You see your own past in a very different light, and Akrasia remains difficult to escape. But at least now you know what you're doing wrong.
Anyway, you've discovered the pleasures of socializing, and you've even acquired an "edge" over those who relied on intuition ever since they were young. What I want us to discuss here is how to reach not just some "proficiency" in social navigation, but actual social excellence. We've collected research on how to be happy, on how to confront organizational problems, etc. I think it would be nice if we also collected data on how to be polite. How to make one's company agreeable and interesting. How to make oneself elegant and glamorous. How to get people to do what you want, and then thank you for it.
Some slight bits of this are approached by PUA methods, but those are very specific in goal and scope, and require a set of skills that can be far from adequate in other contexts (that, and flirting with any and everybody all the time is just creepy and makes you look like a supervillain).
Of course, at its core, social grace is nothing but "intelligent application of the Golden Rule". So, with insight and purpose, everything should be possible... But that's a pretty huge ideaspace, and in day-to-day interaction you often don't have that much time to figure our what to do. Of course, there's rote behavior, protocol, that allows you to free brainspace for what's actually important, but too much of that and it can become blatant.
So... anyone know any actual research on the subject? We can also use some armchair philosophy, it's not like we eschew creative individual thinking here, but some backed-by-evidence stuff is very nice to have.