Hair Dilemma

     Hello bloggers! I have a bit a hair crisis and I could use opinions to help me out. I have been growing my hair out for quite some time now, and it is finally long! The problem is, it is boring. The main issue at this exact moment in time is that it is in dyer need of a freshen-up trim. However, the past couple of times I have gotten that, I still find myself bored with it. I see so many people with long hair that is just beautiful and they can curl it, wear it straight, wear it up, whatever and it looks fine. I can't curl mine because it DOES NOT STAY,  when I wear it straight it just sits the flat, thick, and lifeless, and when I wear it up - well I just don't know a cute way to do it that wouldn't take ages.

     I have thought a lot about cutting it lately and maybe starting the grow-out process fresh. However, me+short hair = not cute. So instead of going drastically shorter, I am thinking about going to a medium length (taking 3-5 inches off) for a while just to give it some life. Any thoughts or ideas? Here is a picture of this mess on my head... maybe you guys are better at picking a fitting hair cut/style for me :) Also if you have straight hair that just doesn't care for curls, do you have any tips for how to curl/keep that curl in? Or do you guys have any quick, easy ways to put hair up that is not just a boring ponytail?? I know this post may sound ridiculous, but hair can make or break and outfit, a look, an attitude and I need some help! Thanks guys!

Please excuse the awkward picture... I don't have any recent with my hair down so I had to take the awkward by myself photo :)