Was walking down the street, when I saw I pretty (fake, but very sexy) blonde girl pass by. I made sure our paths crossed, and as they did I opened as usual with "Hey, can I ask you something?". She took of her earbuds and asked me "What"?

At that point I saw she was a bit younger than I expected, which made me nervous so I bailed. Told her, "Oh never mind, thought you were someone else", and walked away. Not my proudest moment.

Honestly, the whole age estimation thing is one of the most annoying parts to approaching! Especially when you're in your late 20s and want to aim for < 22 girls... In retrospect, she probably even was around that age.. ugh!