Expanding my comfort zone is obviously going to involve doing things that are not very comfortable to me right now. The big example that comes immediately to mind is going to a club alone. Should I treat this experience (and other uncomfortable experiences) like a hot bath, easing myself into it slowly or like a cold swimming pool, just jumping in and getting it over with?

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Some vices miss what is right because they are deficient, others because they are excessive, in feelings or in actions, while virtue finds and chooses the mean.
Aristotle, Ethica Nichomachea

So....my first question here is how would one go abut easing themselves into clubbing alone?

My second one is why would one even consider clubbing alone something uncomfortable?
If you go in with the mind set of 'this is going to be uncomfortable. I'm not going to like this' then of course you're not going to have a good time.
You need to see this as a step, not a step outside of your comfort zone, not a drastic, life-altering thing. Going to a club alone is no big, make friends in line and make friends with the staff for social proof.

Just go out and have fun.

Cinnamon

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Heh, "How does one ease oneself into clubbing?" is the first thing that another friend of mine asked me when I posed this question to him. I hadn't really thought about the logistics of it.

As for why it's uncomfortable, it's because it's completely unknown. I can count on two hand the number of times I've been in a club with friends. I've never done it solo before. I like to dance, but my little experience tells me that I have the most fun when I toss back a few drinks to loosen up and then avoid interacting with people.

So to me, going to a club at all is kind of big and going alone makes the circumstances that much more intimidating and complex. Making friends with people in line seems like a good idea, but TBPH, I'm still learning how to make friends too. (I've had friends before and I have a few now, but I can't really claim I did anything to make those friendships happen.)

EDIT: The more I thought about it, the more I realized that I hadn't really answered your question, Cinnamon. Okay, it's a fact that I AM uncomfortable about going to clubs and there's sure a lot of momentum there for me. But when I really thought about it carefully, I couldn't come up with a good REASON to be uncomfortable in clubs. It's just a habit that I got into and haven't broken yet. Thinking of it that way is pretty encouraging, actually. Thank you.

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Some vices miss what is right because they are deficient, others because they are excessive, in feelings or in actions, while virtue finds and chooses the mean.
Aristotle, Ethica Nichomachea