When Jimmy was a few months old, he had his first haircut to remove his little rattail mullet that was forming. Since then, I have just trimmed his hair in the bathroom and Zach has teased me for doing such a choppy job (I did challenge him to do better, but he told me to just not cut it at all). As much as we thought his hair looked cute kinda long, I just couldn't deal with the bed head any longer. We went to a Great Clips and everyone there was super nice to him so he was surprisingly really good the whole time.
I did kind of hate to see this Conan O'Brien look go in the front. I told her to try to keep it somewhat and not just cut it straight across, but alas she didn't listen. I think before we went I said something about closing your eyes because he kept doing it the whole time and then talked about it (and demonstrated it) a lot afterwards when he would repeat the story to me about how he was a "really good boy." He knew the whole business was very serious.
The most exciting part for him, of course, was the red lollypop he got at the end.