Well, if she's asking for your help, that means she's not having a good time. She might have just been humoring the guy, hoping he'd take a hint she's not interested, then saw you and thought you might be able to help get rid of the guy. You did make a huge mistake there.
You completely screwed up on this one. If you wanted to do something with her on Valentine's you should have made plans. Second, why should she do something nice for you, when from your post says you had absolutely no plans to do something nice for her. Testing the waters isn't asking her to do something nice, it's asking her out.
The fact that you wanted something on Valentine's and were disappointed when you didn't get it shows you do have feelings. Problem is, you've lost your opportunity, you had a good number of opportunities to change this relationship but screwed everyone of them up. Not showing up to her birthday, asking her to do something for you on Valentine's while not planning to do anything for her, not helping her out (as a friend) when she asked you. From your posts there were plenty of times/opportunities to change this, this isn't a case of you being a "nice guy" it's a case of you ignoring missing obvious signals.
Points well taken, and I'm willing to accept the possibility that I was an idiot in the situations.
The reason I didn't show up to her birthday - it was just a gathering of friends from work she had invited, and she had only mentioned it to me in passing. It was at a very fancy bar with like $10 parking and a $15 cover charge, and WAY overpriced drinks. At the time, I had literally about $3, so I wouldn't have been able to buy her any drinks or anything anyways. I literally couldn't afford to go.
As far as the helping outside the work thing goes, again, I saw no signs of anything wrong there. When she asked me for help, she was not in the least bit serious, completely joking in the matter, laughing as she said "come take care of this guy", and when I told her she was on her own, she left on her own anyways, away from the guy. More than anything, it seemed like a friend she was playing along with, and was getting me into the mix. It didn't even seem like a "this guy's creeping me out, please help" in a playful way.
Kinda like if you, me, and a friend of yours go out to a bar. You and your friend are chopping it up, having fun, and in jest you 2 start trashing each other, talking junk and stuff, and you begin to ignore him and start talking to me. "So Nell, how bout them Steelers" type thing.
And again for Valentine's Day, the reason why I asked her what she was going to do for me, well that was advice taken directly from my sister-in-law. One of the pieces of advice that she continues to give me with picking up women is to make them buy ME drinks, make them buy ME dinner. Because if I can get her to buy ME dinner, then I've gotten her interested in me.
My sister-in-law is an awesome chick, who is both the down to earth girl with very good morals, and also the hot chick that'd you'd see out at the bar getting drunk with her friends. Being that type of girl herself, I'd think she'd know pretty well how to get those types of girls (and myself living in a college town and working in a restaurant, those are quite often the types of girls that I encounter).
She basically gives me advice on the types of things that would get her interested in me, if she were one of those girls that I encounter and was trying to get a date with. How I'd go about successfully getting a date with her. Having known her for about 7 years now, and knowing how bad ass of a chick she is, I really wouldn't be doing too poorly to land a girl of my own like her.
Again, I'm completely willing to accept that I was wrong in this situation and I botched any chance with her. I'm not saying I wasn't interested AT ALL. I'm just saying that I never really felt any connection from her, and when I felt there was a slight possibility she might be interested, it was more along the lines of "Why not? I could date a girl like her".
I also know that I sometimes have a problem picking up signals. When I was in high school, I was the complete opposite. I was the kind of guy that pretty much thought that ANYTHING from a girl was a "signal", and I went through some really bad situations with the opposite sex (and yes, I realize they were my own fault).
Now I have gone the complete opposite way. I pretty much don't look into ANY kinds of signals, because I don't want to be the guy that misreads nothing as something. Some of my good friends have told me that I "over-analyze" everything, and in trying not to do that, I miss certain signals that are probably pretty obvious to the rest of us. Shoot, with my last "relationship", it pretty much took her coming out and telling me that she wanted to have sex with me for me to get that she was into me. I had suspicions beforehand, but didn't want to seem like I was over-analyzing and making a big deal out of nothing.