I for one hate chivalry. Holding the door, paying for dinner, etc. It seriously irks my nerves. But thats based on what I believe in. When I put my beliefs into practice i question whether I'm being seriously rude when i walk in the door and hold it open for her as i walk in before her. Its what i do with everyone and i feel that i shouldn't have to treat a girl like she's some religious artifact passed down from generation to generation. it gets painfully awkward when i ask the waiter to split the check. I can't help but look at her face and try to read her to see if she's upset or not. No matter what its always awkward.

What do you guys think? Also are there any things that you guys do to ease the awkwardness of those situations?

You should hold the door for everyone - men and women included, strangers or not. It's common courtesy. It's like thanking someone when they do something nice for you or accompanying a request with the word "please".

Don't ask the waiter to split the check. If anything, take turns paying. I always pay the first time, then the time after if she doesn't offer to pick it up on her own I'll say something like "Do you mind getting it this time?"

This is probably a non-issue. Asking to split the check doesn't affect anything unless she's looking for a free meal.

So stop caring, do it anyway, and ignore the "awkwardness," or write some jokes for those situations to diffuse the tension.