I've been working in offices for the past five years. I worked in retail before that, and that made me more comfortable approaching people; helps to have a purpose to the interaction, I've found. I found retail customer service easier than offices.
In the offices where I've worked, there were lots of people who worked near me, but my job didn't require me to interact with them. Those are the people with whom it's been the most awkward. Neurotypicals seem to like being noticed and regarded, my experience has suggested.
My biggest potential source of social awkwardness is if I'm involved in a group situation, or if I'm somewhere crowded. It's inversely proportional--the more people around, the less I talk. I typically don't enjoy the dynamics of group conversation, but with the right crowd, I'll have a good time. I'm lucky to enjoy the company of my colleagues.
Some people I can converse with, some I can't. I've met really nice people sometimes where their inability to do at least half the lifting in the conversation meant that I had nothing to say to them. I think I'm worst with people who are quiet like me. Actually--the worst is people who really like me and they really want me to like them.
It's an "it is what it is" situation for me. If someone else has a problem with silence, it's exactly that--someone else's problem. If I'm the one confidently carrying myself through my day, comfortable in my own skin, living in the moment in a state of peace, then I don't worry if someone else feels awkward. I felt validated when my counselor told me I didn't have to be outgoing if I didn't want to.
That being said, I do admire the definition of a "lady" or "gentleman" as proffered by Brendan Fraser's Adam in
Blast from the Past: someone who makes those around him or herself as comfortable as possible. I like to be able to do that when I can. I'm learning to appreciate how nice it can make other people feel if I just enjoy the hell out of talking with them.