"You would look good without hair"

I once attempted to compliment a girl's hair. She was complaining that the woman who cut it for her did an aweful job. Apperently it was aweful, almost enough to make her wish she lived in another time period.
This was years ago, when I was shy around girls, and often had difficulties forming complete, accurate sentences. If I managed to do that, my voice would no doubt decide to rapidly fluctuate between Superman and Mikey Mouse. Remember, years ago. Right.
In an attempt to make her feel better, I told her that she would look good without hair. I didn't suggest she shave it off, but I may well have. She didn't fully grasp my clever compliment, and perhaps thought it was an awkward insult. Or, maybe she just saw through my skiddishness, and wrote it off as another random kid learning how to flirt.
I never did learn.
What are some of your lesser known pick-up lines and/or embarrassing talking moments?