The fine art of managing expectations

I have a good friend who is going through a very difficult time and she raised the point that after years of getting her hopes up, only to have them dashed when the results were not as she had expected, she has realized the key to happiness is to not have expectations.  In my very limited knowledge of Buddhism, I think this relates to the idea of non-attachment.  This got me thinking though, how do you maintain hope while managing expectations?  

Countless times I’ve gotten my hopes and expectations up that something great would happen - either a date would be wonderful, I would be recognized for something good I did at work, a night out with friends would be ‘super fun’, etc. And each time I have an expectation, real life seems to fall short. And each time I do not have an expectation and life just unfolds, I am pleasantly surprised.

So I struggle with where the balance is between hope, expectations, and happiness.  Here is why:
Let’s say you are going out for a night and hope to meet a cute guy (a simple scenario).

• If you decide to have no expectations, you are essentially saying I’m not going to meet anyone tonight.  Does this then, become a self fulfilling prophecy because you have already set your mind to the fact that you won’t meet anyone?  Or, does it ultimately make you happier because if you meet someone, that is great, and if not, nothing was lost. 
• Or, if you expect that tonight you will meet someone cool and you do not meet someone, you go home feeling that the night was a failure.

Maybe the fine line is the difference between hope and expectations. Hope that things will unfold in the best way possible (I’m not a fatalist so I will never say ‘meant to be’).  Versus expectations that things will unfold in a specific way, frequently leading to disappointment.  

It is so difficult to detach from the idea of a specific outcome. After all, isn’t that what my expectations of having a family were for the last 8 years?  I dreamt of myself, my husband and our daughter.  Now I have a family, but it wasn’t in the form I expected it to be, and it took a long time to get over the fact that my expectations for my life were not what reality had dealt.  However, my hopes of having a family one day were filled as now I have the perfect family for me - Grace, our dog, myself, my parents, our extended family and our loving friends.  It may not be the mom/dad/child unit I expected but as it turns out, it is much, much better!

This is something I struggle with every day and watch many of my friends do the same.  I’d like to spend more time focusing on my hopes and letting go of my attachment to any expectations of a specific outcome.  I don’t know if this is the key to happiness, but it seems to be one step closer!