i need advice on a haircut should i do it?

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Almost two years ago I had 18 inches cut off of my hair and donated it to locks of love for the cancer patients.. Mainly all children, and it felt really good. The only problem was I was devistated about it. my sister-in-law had talked me into it on christmas eve two christmas's ago, and I did not like it at all. It has taken me this long to grom about 10 inches of it back. Okay so here is the kicker.. I miss my short hair, but I am scared to death that I will cut it again and not like it. Almost everyone I know has went short. My best friend went short and she loves it and looks great, but I am a little overweight and have kind of a long oval fat face and do not know what kind of short cut would do better for me. Does anyone know what kind of cut would do better for my face type? Would you cut your hair short if it took as long to grow as mine? Do you have long or short hair? Would you trade for a day to see if you like it?