Should I cut my long hair?

Do what you want. That's the most important thing here: it doesn't matter what your parents, your friends, your exes, whoever ... believe. That said, I find short hair much easier to deal with, particularly in warmer climates. (I typically grow it pretty long as winter comes (for warmth) and then chop it off with the advent of summer.) You sound like you're quite fed up with your long hair. And personally, I think that if any part of your hair is thinning (defined as "people can see my scalp"), it looks a bit desperate. You might as well get it cut nice and short, military style. As for how to describe what you want, well: it's probably easiest to print out a picture of someone with hair that looks like it might work on you, show it to your barber, and say: "Cut it like this." Google Images is your friend. Common short styles include the "https://en.wikipedia.org/wiki/Crew_cut," and the "Caesar" (in the late 1990s it was also known as the "Clooney," after the actor George Clooney). The terms described here might help as well: https://en.wikipedia.org/wiki/Regular_haircut.

I got this a ton when I was starting out professionally. I used to wear a pony tail nearly to my waist, most often braided.   In college, I will never forget CompSci 101. The teacher told everyone in class to stand up, then, he said "If you have ever used a computer, stay standing, else, sit down." A few people sat down.   Then he said "If you are comfortable using a computer, stay standing."  More people sat down.   Next he said "if you own a computer, stay standing." Most of the class was now sitting.   Finally he said "If you built your own computer, stay standing." Three of us were still standing, all with long hair in pony tails and glasses.   Long hair was an identity thing for me for a long time. It seemed to be an in thing with the professors and a lot of the professionals. That changed over time though, and as I got closer to business and further from writing code I heard a lot more "Get a hair cut."   These days, I keep things short, and lightly spiked forward. I tell my barber to use clippers with a #3 guide for the sides and back, then feather the top in at a reasonable length. It took me a while to be comfortable that short.... I started with a look that was longer, but in the end have found this to strike the right balance for me.   Do I miss the long hair? Yeah, occasionally I do. It's a pain to grow out and goes through all sorts of awkward phases while it's growing out... I don't think I'd be willing to go through that mess again. In general though, I get more compliments on my appearance with short hair, and it's way easier to take care of.

Yea, you'll save on shampoo and you'll save time in dealing with your hair. It is certainly cooler in summer. You can play around with hairstyles. You can always grow it out again. Sure, go ahead. Cut your hair. Whoa! Slow down there young man. You do know that cutting your hair can have consequences, do you not? Do you know the story of Samson? Here's a condensed version: Way back when, Samson was a tough guy; dude had like super powers. Seems that he made some deal with God about cutting his hair. One day Samson meets Delilah. Delilah is what is known as a major babe. (Yea, I'd do anything she asked) When Samson rejects the love of the beautiful Delilah, she seeks vengeance that brings horrible consequences they both regret. Think twice about cutting your hair. Sooner than you think, you will have no hair to cut. The story of Samson and Delilah has been the subject of pen, screen, and stage for many years. Painting- by Peter Paul Rubens (1577–1640). It dates from about 1609 to 1610. Screen- The 1949 movie with Hedy Lamarr and Victor Mature Under Boob Alert! Song - Perhaps the most famous version is by the "You can shave my head, clean as my hand And my strength will become as natural as any old man." For more on the Samson and Delilah story: http://en.m.wikipedia.org/wiki/Samson_and_Delilah The Bible has this story: http://mobile.biblegateway.com/passage/?search=Judges+16

I had hair down to my shoulders until I saw a video of the top of my head (which was going bald), and I got a 1/4" buzz cut the next day.   Long hair accentuates your baldness, imho.