I ran into the same problem after I got a bob, one side would curve in towards my face and one side flipped out at the ends. I blow dried with a brush, without a brush, flipped my hair upside down, etc. A flat iron helped but I am hair-challenged and at best could get it to straighten but never curl inwards.
The last time I went in for a trim I asked the hairdresser and she said it is a weight issue, I guess because the hair isn't weighed down anymore? I don't know, but she put a few layers in it and evened it out a bit. I'm trying to grow it out and it has gotten to shoulder length and is finally not flipping out.

The problem is, now it is annoying so I put it in a ponytail all the time again. haha
Another option is to work with the flippies instead of against, style it so it flips outwards all around and put a texturizer in to get more of a tousled look?