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Halloween is all about friends and having fun. I've never had a bad time on Halloween. Christmas on the other hand is a mixed bag for me. I've had some great Christmases and some terrible ones. It's great to see extended family that you don't see that often, or gathering with your friends to exchange gifts, but too many times weather and people getting sick have fucked up the plan.
There's just something about staying up and drinking a mulled wine or a peppermint spiked hot chocolate or a real eggnog with rum with a loved one. Every holiday is a drinking holiday when you're an alcoholic!