(Or he, the concept is not gender specific.)
That expression is very revealing. First of all, it's all about the shallow. You never hear "She's out of your League" when talking about an ugly, but incredibly nice girl. Similarly, you don't hear that about poor, short men. I don't care how nice the guy is.
So, when someone says "out of your league", it means:
- The person speaking it is pretty shallow
- They think the attractive person is just as shallow.
- They are surprised you are not as shallow.
Now, it's OK to be shallow. But it's not OK to only be shallow. You need more.
The concept of "out of your league" is at heart an extremely cynical, shallow idea.
I want more - for me and everyone else.
When someone uses that phrase I lose respect for them.
Every single person should think no one is out of their league. More importantly, it is true - as long as your potential date is not shallow.