As a general rule, drinking alone is a bad idea. A glass of wine with dinner or a nightcap, sure. But a true evening with a bottle of Scotch as your only companion will usually lead to a bad place where the tears go down with the whiskey.
There are, however, occasions when a girl needs Jack, James, Jim, etc, and no one else. One is heartache. You were going to have tears anyway, so may as well make them taste good, especially if the non-liquid form of Jack, James, Jim, etc was a total bastard as they probably were. It’s less fattening than ice cream, considerably warmer, and a good cry can be a good thing – just stop the drinking in time to not have to resent human Jack and liquid Jack on the same morning.
The opposite of this is celebration. Not the birthday celebration or anniversary celebration (for God’s sake), but the personal victories we have in our life. When I moved to New York on my own, my friends in Boston gave me a nice-sized bottle of Gentleman Jack. I was trying out NY for a year and trying out my independence. I had myself a drink the first night in my Brooklyn apartment, sleeping on the floor with all my possessions falling out of boxes around me. I had another swig when I put together my bed on my own (I didn’t say well, but it sort of held up under most circumstances – damn those Ikea slats). Another drink when I sold my car, when Obama was elected, when I got my first travel writing piece published, when I started dating again, when I moved into my second Brooklyn apartment, and finally, finally when I got a job (other than in a coffee shop) a little past my year deadline. I guess you could say I drank my way through my first year in NY alone – but it was just the one bottle.