Okay I gotta step in.
>Advice for Teenagers: Watch Teen Romance movies.
Ok, I understand my advice is a bit cheesy. But, i'm not a teenager.
Teen movies are movies, bad ones at that. How often do you see the cheerleader fall in love with the nerd? Teen movies are BAD places to look for advice when it comes to dating.
>If you've been rejected twice, you're most likely asking girls waaaaaay OUT OF YOUR LEAGUE.
Dating is a numbers game. Getting rejected twice(by different girls, its futile to ask out the same girl twice) is no big deal, it happens. If it is like 8 times, you should take a look at your method. You should drop down a level to make things easier, but you have to stick to it. Re-evaulate your approch, it could have been that you did something that turned her off. If you are more sucessful in the lower level, apply what you learn to better looking girls.
>PROTIP: Draw your inspiration from the weather when talking to her.
The weather is a boring,cliche topic. Just use your environment to your advantage. See her reading a book, ask her a question about the book. Find something she has, is doing, or is with. It may be hard at first and scary, but if you can carry a conversation, then you will be fine. Warm her up to you, and don't forgot to end it with her phone number.
>Do not make assumptions, an example of this would be thinking the girl might not like you because she's too pretty or if she's really hot that she might be taken.
Truth to that. Never be afraid to take a chance, in fact don't even hesistate.