Have you watch Josh Waitzkin's "The Art of learning", I think he would explain how chess and relife relate to one another better then most.
On chess and life

Do you believe that understanding of chess and (real) life go together?!
That all depends - for starters, on how you define "real life"

1. Chess exists within the greater category of life.
That being the case:
a. There are ideas and skills learned in areas of life that can be transfered / applied to other areas of life. (life -> life)
b. There are ideas and skills developed from studying chess that can be transfered / applied to other areas in life. (chess -> life)
c. There are ideas and skills developed in other areas of life that can be transfered / applied to study of chess. (life -> chess)
d. There are ideas and skills learned while studying one area of chess that can be transfered / applied to other areas of chess study. (chess -> chess)

i think that some concepts of chess can be applied to dating.
in chess it's well know the concept that one bad move nullifies 40 good ones. You should do positional moves, calmly improving your position, rather than embark in risky and silly actions.
in dating, only one single slip up will lose the girl instantly while simply being careful in not screwing it up (i.e. blundering) will go a long way.
Similarly, instead of going for risky attempts such as trying to impress her with how much money you make/how intelligent you are/bragging about how many friends you have, etc. that might in a limited number of cases be successfull but it is also likely to backfire, being calm and cool and not saying much (i.e. positional moves) is usually best.
Do you believe that understanding of chess and (real) life go together?
Please check this out:
http://www.alinalami.com/2011/05/luzhin-defence.html