The Story of Anna or Stupid Circumstances!

As promised and much anticipated, here is the story of Anna, who if you remember I saw getting on a bus Sunday morning to begin a 6 month adventure in central America. She is also a friend of Dave's who happened to get hired at the bus depot (where I work) over the Christmas season. There were actually 3 of Dave's friends who all got hired at the same time. Seeing as how they are Dave's friends and all I took it upon myself to hang around and show them the ropes... well... sort of. Mostly I was just operating in my typical goof-ball mode. We all seemed to get along pretty good and I was soon asked to tag along with them to the Toad and pose as someone named JC. The elaborate ruse came about because the event at the Toad was a surprise for someone. Anna had used the excuse of having a fictional date with someone named JC as her excuse to not hang out with the focus of the surprise party. It therefore stood to reason (to whom I don't know) that I should pose as JC. Kalyn (the other girl from the depot) and Anna decided that I should act like a real dick to see what their friends would say. Even when acting, I can't be a dick... well... to pretty girls at least. Did I mention that Anna was attractive? Strangely enough she didn't really fit into what I usually find attractive in a gal. (ie. glasses and medium length hair... I'm sure that there is something in that fact... maybe I am secretly in love with myself and the only girls that "do it" for me are ones that look like me...???? hmmmm.... There might be a thesis in there somewhere....???) Anyway, this girl Anna is kind of a hippie, at least in appearance, even sporting dreads. As per usual, I busted out my typical goof-ball charm and things seemed to go pretty well with her. Taking the next logical step I asked her if she wanted to hang out sometime to which she agreed. Funny story about the way I did that too... She was pondering taking a double shift the following Tuesday because she rarely had anything to do at nights, to which I stated "I can't stand idly by as someone works a double shift. If you hang out with me that night then you'll have something else to do!" (or at least something to that effect). That approach seemed to work and the following Tuesday we hung out watching "Transformers: The Movie" and then going to the Toad to meet some of her friends. I thought that I had done pretty good on the whole excursion because she spent a lot of time talking with me instead of her other friends. She even added me to her contact list on MSN immediately after I dropped her off. This was notable because I had only passingly made note that I was on MSN right when I picked her up to begin with.
The next couple of weeks were the Christmas season and it became really hard to get a hold of her. I tried calling a couple of times but she was working two jobs at alternating times of day. I was able to talk to Kalyn a bit and she seemed to think that, while unsure as to what the hanging out was, Anna might have wanted it to be a date. Despite Kalyn saying that she was rooting for us to hook up, it took a couple of weeks before I was able to schedule some time to hang out with Anna again. Four days before she was leaving for Central America for 6 months. At this point I figured there was no real point in "making a move" so we just hung out and watched "Back to School." (she was super busy so only had a couple of free hours to hang out) She had a going away party at the Toad (recurring location here) a couple of days later which I attended. The only problem there was that she was sitting a few seats away from me so I couldn't bust out the smooth. When I finally did get a chance to talk to her, it was near the end of the night. During a conversation about how both her and Kalyn had had someone try to pick them up at work (Anna mentioned someone other than me which confirmed my thoughts that she did not know what my intentions were) I decided to just came right out and say what I was doing. I said "to clear up any confusion, I was indeed trying to pick you up, I just suck at it." Then I said that when she got back I would take her out on an actual date. The only thing I am mulling over is whether or not I should have tried to give her a kiss before she left. I am not the kind of person who is super forward or anything, I usually try to gauge the "vibe" before taking a step like that. I didn't make the effort with Anna... should I have???? I don't know...
Long story short, in 6 months baby! I got a date!