Dating Beyond Your Means

We all have had that friend who thought he’d landed himself a beautiful girl… a girl who even he thought was above his reach.  He would go all googly eyed and stupid around her.  He would brag about her to all of his friends.  He would talk about marriage.  Then she’d dump him and he’d be heartbroken.  He was just a passing interest for her.

So the question is: Should you date someone who you think is a level above you? Someone who is a better overall combination of looks, personality, intelligence, money, charisma, and sex appeal?

I mean we have all seen the ugly girl with the cute guy or the retarded guy with a smart woman and wondered, “What the hell?”  We have seen our friends with either a person we considered significantly above or below their level and shaken our heads.  Rarely are our expectations of their failure disappointed.

I have never dated a girl who I thought was a level above me… perhaps I have some insecurity that keeps me from really going after one… or its just that my ego is so huge I think everyone is under me lol.  A combination of both probably. Hypothetically, is it worth the high rejection rate and potential pain to pursue someone you think obviously outclasses you?