I've spent the majority of my life pretty much solitary, with a select few friend that I could be comfortable talking about anything. For as far as I could remember, I've always struggled with interacting with groups of people, and ended up as the guy you wouldn't invite to an event or social gathering. Not because I was awkward, or said the wrong things but mostly due to being the silent type at group gatherings, and often enough, challenging and questioning peoples perspective, which ultimately lead to negative emotions/reactions on their part. And in this day and age, who feels comfortable being judged or challenged on their beliefs ?

Once I've started working in bigger groups of people, I tried to somehow change the way I interact with people, trying to be less judgmental, attempting to get to know them, ask questions about their life, but somehow, I always end up leaving a bad ( from their perspective ) impression. I dont joke around in new groups as I would with groups of friend, due to lack of comfort I guess. I'm reserved, laid back, observative and only speak when I have something meaningful to say.

This kind of attitude would work with people that share the same worldview as myself, but how do you deal with the other 95% ? How do you get to be accepted in new groups, integrate or climb the groups social hierarchy without being a try hard ?