You said your from Asia so their may be a little difference in conversation flow .
I would shorten that opener down as much as possible and as the guy asked above are you a Shakespearean..... cool it up a bit.
Instead of
Quote:
Well, a friend of mine who is almost 40 years old is really into his female co-worker. This poor chap has not dated for almost 20 years and has had only 1 girlfriend in his life. (Creating intrigue and controversy) Well, he told me that he has written 11 letters to this lady and hopes to win her over, but the problem is she has NEVER replied. He wanted to write her another letter because he believes that females appreciate that gesture. But I think that it's not a good idea because that would come off as stalkerish, sending 12 letters. What would you advise?
I would say " friend of mine has been writing soppy letters to some girl ( dont use the word female or lady ...ever

) .....declaring his love and that .Hes like written a books worth of them ( over exaggerate it too add some comedy maybe even gesture the amount) The thing is she never replys to any of them .. and yet hes like addicted to sending them to her . If a guy did this too you would you respond , or just laugh at him ?"