What should I do with my hair right now?

Hey guys. So, for the past few months, I've been trying to grow my hair out, and I'm pretty sure I'm right in the middle of the "awkward phase" because I've been having a lot of trouble deciding what to do with my hair lately.

Here's a picture from the front, here's one side, and here's the other side.

That's a few minutes after I got out of the shower, that's why it looks wet.

As you can see, right now I'm just kind of sweeping it off to one side and hoping for the best. Ideally, I'm going for a look similar to this picture, or this one.

So basically, here's what I want to know. 1) Can I pull off a long hair look similar to the ones in those pictures? I've never had my hair very long before and although I'd like to grow it out at least once, if it just isn't the look for me then I'll just cut my losses (heh) and go back to short hair. 2) How can I style it right now? I don't have a huge problem with the way I'm wearing it in the pictures but I feel like that big swooping wave in the front is kind of weird looking. And finally, 3) What should I tell my hairdresser to do in order to achieve that style? My hairdresser is actually my best friend's mom so I don't have any problem talking to her, I can basically just pass on anything you guys tell me to her.

So, thanks in advance for any help. I'm more than willing to post more details/pictures should you need them.