To try to chat someone up who is a bit too good for you. usually seen when a ginger headed dork is doing quite well with a blondie in a pub, while his much nicer friend is getting fuck all luck.
When someone (or something) is out of the class of people you are expected to date. This includes an individual who is too attractive for you, or a person who is too unattractive for you.
A way females can say that they're better than a male without saying they're better than a male. A passive aggressive way of saying she's too good, better than, beyond his realm.
When a girl/boy is much better looking and often more experienced than you are at dating.
Therefore you must work your way out of the lower leagues in order to achieve the 'premier date'. This is because the only way you can become as good as him/her is to gain as much experience as possible in the hope that you get to beat them in the future...
Friend 1: "Wow that girl is so out of your league"
You: "Yeah, that's why I'm starting with this" *points at lower, less attractive and overall 'easier' woman.*
Friend 2: "Fair enough"