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Post straightening, I still want to chop all my hair off

I’ve been on a little vacation (I’m STILL trying to get used to using that word instead of “holiday”) to Maui in the past couple of weeks, but let’s talk about the most important things first: hair cuttings.

I have the kind of thick hair that makes anyone tasked with blow drying it shudder. Biceps and triceps quiver at the prospect of an hour’s worth of battling with my mane. And even that doesn’t promise the smooth, sleek outcome from the magazines.

It is resides in a strange place between curly and sort-of wavy. When it’s longer, it’s closer to a normal curl for about 20 minutes before it starts to shoot out directly sideways from my head.

If I leave it more than four months between cuts it becomes a tangled mess of grown-out layers that knot approximately 2.5 minutes after I’ve brushed it (that is if I ever actually feel like incurring the tennis elbow it takes to brush it out).

Don’t even ask the shorter styles. I’ve cut my hair to about shoulder length maybe three times in my life. Each time was a disaster of frizzy proportions. There are always tears and a rush to pile as many products onto my head until the haircut had grown out.

But my teenage years are well behind me and I think it’s time to dip my toe into the murky waters again. I’m tossing up between a side or back undercut and going the chop.

I’ve been really wanting a bit of an undercut for a while now and I figure now’s the time to do it, since my job at the moment seems like it would be a bit laid back about that stuff. But then I could always chicken out of that and go shorter.

Which hair? One, two, three or four? I can’t choose!

Do you have nightmare hair and have you tried any of these styles? Help me out! How did it go? What should I look out for?