Flirting is an art.
Successful flirting requires the right amount of confidence, patience, and intuition about how other people are feeling. If you come on too strong and can't pick up someone else's vibe or body language, it can get creepy fast.
But if you don't lead with some confidence, it can just come across as awkward fumbling, and the flirtation attempt won't take off in the first place.
When I was 15, a 13-year-old boy came up to me and offered to show me his rock collection. Then he asked if he could see my boobs. I politely declined the latter request but the rock collection was pretty cool.