Why is it so hard to say "Goodbye"?

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I am so bad at saying goodbye for so many reasons. Some people are good at it. For one, I attach myself emotionally and I find it hard to express my feelings to the person who is about to leave. I find it hard to say what I really feel even though there might not be much to say other than "Best of Luck" or "Keep in Touch". I wonder if that person will be okay and if they'll make it in their new surroundings. No matter how close or far they'll be, it always break my heart to know that someone i see all the time will be leaving and I probably won't see much of them depending on where they're going. How do you deal with saying "Goodbye" to your friends or loved ones? Does it get easier for you?