I'm not a hair expert but feel qualified to comment on the flippy hair issue, and the flat on top issue, as I've had both, and so have my DDs. So I have come to believe that is a cut issue - not a hair issue.
San, if you can find a Vidal Sassoon salon or trained hairdresser, I highly recommend. Their philosophy is that it is all about the cut. The cuts are "precision" cuts and you should theoretically end up with a wash-and-go cut that looks great air-dryed, or blown dry without much need for product. They purposely work with your hair, not against it.
It appears to me that your hair is not really straight as a stick: it has some body and bounce and wave. Does it curl or wave more if you let it air dry?
I do think a choppier haircut will help with the flippy issue. Bobs that are blunt cuts with very little layering usually result in flippy issues and cowlicks showing up in weird places, if you have any bit of wave at all.
As Ana suggests, you might even benefit from a bit of razoring. I don't care for this on my hair because it's very fine and just ends up finer- plus grows out awkwardly. It is best for thicker hair, I think. But it could work for you. I guess I should add it has worked great - but only if the hairdresser is very judicious and razors just the front a tiny bit - and does not razor all over.
Better than razoring is when, at the end of the cut, the hairdresser goes piece by piece - that has been cut straight and even - and cuts in little nips (I have no idea what this technique is called). Sometimes they use special scissors. But it's not razoring. Ana - do you know what this is called? This is what I think gives the choppiness and makes it different than a blunt cut.
Flatness on top: if you mean at the crown, you need shorter layers in the back. Really short. This will give you more volume and height at the crown. For example the layers at my crown are about 4 inches long, and the layers underneath that are even shorter. This is what I was referring to on another thread as a "graduated" bob. It has lots of layers in the back, but is kept longer in the front. Depending on how much you angle from back to the front you get what is known as the Pob (Posh's Bob). The angling is critical and should basically follow the line of your chin, with the front part an inch or even two longer than your chin. Posh's angling is very dramatic. I've had that cut too and it's cute - but I find I need to flat iron to keep the front part straight.
If you don't angle quite so dramatically, you get what you found on hairfinder - which is nearly the same cut I have right now. I can (and frequently do) tuck behind my ears for different look too. At that length, you can go all piecey if you like - but it requires pomade or something similar applied just to the ends to funk it all up and make pieces stick out this way and that.
Another question for you: when you leave the salon, is it flipping out or perfect? If it's only when you try to duplicate back at home that the flipping starts happening, then you probably need to practice your blow drying technique. Every time I go to the salon, I watch carefully and ask numerous questions. I've slowly improved my blow drying ability over the years. Do you have a super large, round brush with metal and vents? That is the best type of brush - even for short hair, not just for long hair.
One last thing: your part. Have you every tried a more dramatic part - farther over? Or does your hair just always naturally want to part the exact same place? Or have you tried an uneven part? Uneven - i.e., a zig-zag part - are are great - especially when dyed hair starts growing out. Hides the roots and also adds some lift too.
The Meg Ryan do is adorable too and I really like that option!
