when do you let go?

first i want to mention that i just learned how to use predictive text on your phone and it is pretty great.thank you jason.you know that i love you and you were right.so when do we let go and stop trying?for me that has been the million dollar question lately.i met someone that peaked my interest like few have but i just dont know.he is smart, seems to have a sense of humor that i would enjoy, goal oriented, simular values, just so many qualities that you just cant overlook but the timing just is off.its like i dont mind putting myself out there if there is real interest otherwise i feel like a pathetic fool just because im being me.