Do I feel comfortable doing that? Not always, but I do it now and again. Even in the mommy world, I don't always feel like I belong. But it does provides material for some great stories. The most comfortable social interaction is with other writers. Why? Because they get me (for the most part, I might have some quirks, but don't we all). They know what it's like--the feeling of the good and the bad times.
Conferences are good, but can be expensive and overwhelming especially if you're shy. Are you? No worries.Check for local writing groups or book clubs and bring someone you know. They are a great way to get out and meet people and usually are less crowded.
For example, if you are in the Philly area there is a Philly Lit Meeting this Saturday (21st) check out the info here. There's also a Philly Book Club meeting on the 22nd. See? Events.
All you have to do is research.
My thought is that it's healthy to get out and speak to an actual human. Trust me, I have characters speaking to me all day (besides my kids) and I need some reality check.
Any events you are attending?
Tell me if you like to socialize?
Have a great day!