why does he always ask to split all of our dates?

It's not exactly the norm to pay for the woman's dinner anymore. So he's probably just thinking that you're a modern woman who would feel insulted if he insisted on paying the bill himself.

Hard to say. Only he would know.

It could be because you both work and that he feels like you should be able to take care of yourself.

Does he do other gestures though to show he cares?

Paying full for the bill doesn't really mean all that much. And it is his money so paying for his own cigarettes isn't a bad thing Lol

What's wrong with splitting the check...

I've heard complaints from single women lately that lots of men don't pay for dates anymore. Not only that, the men mooch off of them for the duration of the relationship.

It could also be a gender-equality issue. I think some men are beginning to resent the "treat me as an equal but you get the check" dichotomy.

Maybe he really can't afford to take you to dinner. If he can, have you asked him why he doesn't treat?

A real man a gentleman will always pay for the lady. Unless she is asking him on a date an tell's him that she will pay everything. But he sounds like a mooch and they often attend to think of them self long before others.