I dyed my hair for the first time when I was 17. Pitch black. I loved it.
I continued dying my hair all through college-- not often, but maybe 1-2x per year.
6 weeks before my wedding, I decided it'd be nice to have red highlights when the sun hit at my outdoor ceremony... bad idea. Somehow my hair turned orange with a dark brown/red highlights color. It took 3 visits over the next few weeks to get it back to my natural color before my wedding day... and a TON of cash. So, the last time my hair was dyed was over 10 years ago, September 2004, just weeks before I was married.
I'll be 35 in a few weeks. have a sprinkling of gray hair.. a few for every couple inches of air I have. I've been thinking more and more about whether or not to dye it, or let it go natural. I love my natural color and want to keep it as long as possible. I also want to know at what point I'd be completely gray... if I start dying it, I won't really know when that is or what it will look like. Letting my hair naturally evolve into whatever comes next feels like the right move for me... but I'm nervous about looking older, sad about losing a color that's been mine for 35 years, and a feeling the pressure from societal norms to just dye it... and frankly, I don't want the expense.
I guess I'll take it one hair at a time. What I do know is that I don't really want to grow it out after dying it... it's just not as graceful to see that exact beginning and end.
I hope I'm brave enough to go where my hair takes me.
Update October 2015: I dyed just my roots in time for our anniversary... so I went a good 11 years without dying! And I'll be 36 in a week.