This a tough one, it's all over the map for me. However, based mainly on your This or That section, I'm going with Desmond . He seems to fit well with the optimism/pessimism thing...it seems he's always really excited and hopeful about something (like seeing Penny again) or he's all mopey getting drunk on the beach. He also strikes me as disorganized, but I can't hold that against him because I imagine being flung through time does scramble your thoughts a bit. I also imagine after his time in the hatch he would also have developed a rather strong aversion to slow computers ;)
Charlotte. I had to really consider this, but... I think you're too introverted for Charlie, and Desmond isn't exactly aloof. So, Charlotte is intellectual and reserved initially, but has the ability to get things done and take control when necessary.
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