So the social pressure of 'getting a good haircut' is starting to build up around me and my gf's parents are also starting to get a little annoying telling me how much a good haircut would improve my looks. I've been doing the easy thing so far rocking fairly shapeless longer hair which is ideal because I don't have to worry much about anything and can handle upkeep myself. But it really doesn't look to grown-up and mature. So I figured it's time for me to take it to the next level and become a respectable adult.

It's also a bit scary though because I'd need a style that doesn't arouse too much suspicion and ideally lets me cut my own hair myself without being too difficult. I'm also not a big fan of super-tidy hairstyles. And I'd need a cut that still disguises the piece fairly well. I'm a young guy so density isn't too much of a concern.

I was hoping you guys have styles you could recommend or suggest?

Would it be too strange for me to get in touch with a normal hair cutter and be open and upfront about my wearing and him have him cut it in for me? Or would the risk of them ruining the piece be too high?