Now, let me rephrase your statement as I see the world.

some things CAN BE negative and some things CAN BE positive, its about recognizing Your CONTEXT of the situation.

Even things that appear as negative to everyone sometimes have positive implications.

John has been sick for nearly 3 years. His pain created a life of misery. John died, his pain and misery is over. His loved ones are no longer forced to watch him decay.

Even natural disasters where many people die can be positive when considering the larger issue of over-population and food scarcity.

I won the lottery, oh happy days ahead. Until taxes come out and the money is gone again. All the partying that was done caused health conditions you can now no longer afford to treat. You lost some really good friends along the way because of your indifference and narcissistic manner.

When assessing another person I try to remember that I have not walked their path. All I can do is assess how they are to me right now. Once they establish a pattern with me, then I determine if they are positive or negative.

But what if I like playing handicap games? hehe.

Looks like you could play that one on your own!

I always thought that phrase was based on the physical looks of the couple? One example is the sitcom "king of queens" the wife's character(Carrie) was pretty, petite & fit. The husbands character (Doug)was overweight, & sedentary. In the real world Carrie would have been out of Doug's league, bc of the disparity in their physical appearances.

Isn't that how men in general try to figure out how to approach women, the women who look like models don't get asked out by the guys who look like shlubs...the men avoid rejection that way...

Colloquially in American culture the phrase is typically used as a sports analogy. Suggesting that like in competitive sports, when engaging in romantic pursuits, those that possess certain attributes are more desirable than others.

It's a grading/classification/filtering concept... and usually very subjective.

Like others have said here, it's mostly a reference to a judgement of apparent compatibility. Appearances can be deceiving.

Being out of someone's league can be rooted in :-

1. esteem /ego issues
2. perceived incompatability in areas deemed important.

People are gonna define the term in different ways, but the feeling on the receiving end is generally the same.

This has something to do with your self esteem i guess. I dont thunk a person would pursue someone if he/ she thinks they cant reach that person from the beginning. It would be a bad start. It's a matter of how confident you are on handling a situation or knowing a person or seeking what u really want. I dunno. Just a thought.