What Cell Phone Should Drew Get?

On Christmas, I will reach a pivotal point in my life.  Decisions will need to be made, and I'll have to live with my choices for at least the next two years.  I need your help in making up my mind!

My cell phone contract is up in just over a month.  Rather than just getting a new phone, I'll probably be switching carriers to be on a family plan with my fiance.  I'll be switching from Verizon to T-Mobile, and I have no idea what kinds of phones they have!

Obviously the iPhone is super-trendy, but it is worth the money?  I've had a Droid X for the past two years and it's treated me just fine (for the most part).  Plus, do they even offer the iPhone on T-Mobile to begin with?

Also, I might not even get a smartphone.  Data plans are expensive, after all!  Are there any good phones out there that aren't smartphones these days?

I'm so lost and confused!  Please help!