I highlighted my hair only ONCE in my life. I have really dark (practically black) hair... so I basically have to strip my hair to make it another color.
That said, I got really awesome orange-y red highlights my junior year in high school. I LOVED them. THey didn't look weird or anything.. they looked really good...and I had cute short hair at the time. I would have kept them going, but it was too high-maintenance for me, and I hated to think of what I was doing to my hair (stripping the color) for the end results.
I haven't got it highlighted since, and people always compliment me on my gorgeous locks
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