One thing that I've found that works when writing dialogue is to read it out loud to myself a few times, to figure out if what I wrote is something that character would actually say, and if the line that comes next would be a feasible reaction. I'm gonna start writing a short scene for a film class soon, and hopefully having actors read some of my writing will help me figure out where I'm at as far as emotion in my dialogue is concerned. Now for me to find something that I'm actually qualified to write seriously about without looking like a prick.
As for being able to connect with characters in stories, I've found that the actual personality or circumstances the characters have mean little in the long run. Being able to understand and relate to someone's writing is a deeply personal and emotional experience, I think, and not something that can necessarily be forced by either the artist nor the audience, nor can anyone explain it without someone else having a completely different opinion on the matter. All the artist can really do is write what he feels, and hope that his audience will experience it with an open mind. And of course, context has a lot to do with it as well. In theater appreciation class, I learned that in ancient Greece, theater was supposed to be both cathartic and educational; meant to entertain while also giving the viewer a glimpse of themselves. Often I find that all well written stories are this way, and while the standards for what makes good art may change over time, that basic concept is what good writers should try to go for.
On an unrelated note, what is the best time for you guys to write? For me, all my best work comes when I'm highly emotional about something. I've recently looked back at the things I've wrote thus far, and all the best work was made during times when I was truly upset about something, or otherwise excited or caught up in one thing or another. On the other hand, in times when I've been relatively content with myself, I could hardly find any words to put onto the page at all. So I've decided that from now on, I'll always keep myself occupied with one thing or another, so I won't get bored with myself. But what I'm afraid this has resulted in is me being really enthusiastic about creating something, but not knowing what it is that I should actually create.
Welp, I'm just repeating myself now, aren't I? Sorry about that.