I was 16 when I first thought about shaving my head. Back in 1980, that wasn’t a popular thing to do.  I finally shaved mine 35 years later. 

Five years ago, when I was 59, had been thinking about trying a buzzcut just one time. Once my (then) girlfriend said ok, just once, we met my neighbor at a city festival. He is bald and had a fresh no guard clipper shave that looked great. I also noticed at least a dozen guys with shaved heads. So early the next morning I got the clippers out and did a buzzcut, didn't like it so clipper shaved it. Well, I thought it already looked shaved, so I jumped into the shower and razored it bald. When my GF got up, she was shocked. By that afternoon she said I should keep it shaved, and she loved it. Within a few months she decided I should grow my hair back, but I was hooked on the shaved head. She's long gone, and I still enjoy the bald look.

When I was in high school some of the guys on the football team got buzz cuts. I wanted to get one but did not have he nerve. In my late 20s I got a couple really short fades type cuts and can remember my boss in San Francisco saying you need to grow your hair out. Started getting flattops in my mid-30s.  Always had short hair since. Started shaving it off once a year in my 40s. I 've been shaved now for a couple weeks and keeping it off.

I wanted to get really short buzz when I was 17 (1948) and did so when I was 19 (nickname: cueball). seriously considered shaving it 1953.  Did so 25 years later before the style became more common.

I was 8 years old when I first fell in love with shaved heads, I had a student teacher in grade 3 with a shaved head. I buzzed my head when I was 13 and it looked horrible which held me back from shaving my head. I had blue hair for several months last year but needed to buzz it off as I was going to TV show tapings in New York City and knew I needed to buzz it off. After buzzing it, I thought I would shave it off completely and if I didn't like it it would soon become a buzz cut.

Side note: It's been 2.5 months since I started shaving my head and so many people have come up to me and told me that I look much, much better with a shaved head. When I show comparison shots, people are like "Don't grow your hair back." It makes me feel so good to hear that!

Probably in my late 20's or early 30's.  Prior to that, it was very unusual to see a guy shave his head, so the thought really had not occurred to me.  Once I saw a few in real life (vs. TV and movies), I liked the look.  I also never really liked my hair, even though it was thick.  So I really decided then that I would rather shave at the first sign of balding, which I did in my late 40's.  I wish I had just done it sooner since I like it so much more than my hair.

When I was a kid I would get buzz cuts. When I was in 8th-grade biology I remember learning about genetics and that baldness was an inherited trait. I told myself that the day I find out I'm going bald I would shave my head. When I was 25 I was getting a haircut and the lady told me I was starting to thin. At that moment I told her to shave it all off and I never looked back.

How did she react when you told her to skin it?