Immaculate mate, get the words 'out of my league' out of your vocabulary.
Those words are the things which create the league in the first place.
Be comfortable in your own skin.
Don't seek approval.
View yourself as the ultimate catch
Get your game together in all ways.
Then if Jennifer Anderston happens to be about at the time go and give her a chance to get to know you.
You've got to BELIEVE it before you'll see it. Confidence is the most attractive thing to women and if you believe she's not in your league then guess what - she isn't.
Anyway I'm really glad you've found your ability to laugh at the whole thing. Now that's good. Because you're now officially a better man than you were when you first posted this thread. When you are so detatched from the outcome and your previous mistakes that you find your previous mistakes hillarious you've made the psychological shift that will really improve your game.
Learn from your mistakes, laugh at them - learning is fun, and know deep down that you've GAINED from the experience. If you do these things you're on the path.