This girl I work with asked for my number a little over a month ago only because I am good-looking and an older man. Because I'm an older man, though not much older (she's 18 and I'm 23), I think she had expectations that I would know what I'm doing, but I didn't because I have very little dating experience. We went out on 2 dates and, well, I wouldn't consider the 3rd a date because, after the 2nd, I think I switched off all attraction. She may have been giving me one last chance (I'm not trying to sound like a needy wuss, but in her mind, this is what I think she was thinking) to see if I would be different on the 3rd date.
You see, I'm shy, but this didn't mean the conversation went terrible on our dates. I mean, yes, she led the conversation most of the time on each date, but there wasn't a whole lot of awkward silences. I asked her quite a bit of questions, maybe too much. Anyway, on the 2nd date we went to a drive-in and cuddled, but I didn't kiss her because I supposed I wasn't sure if she wanted it. If a girl is willing to cuddle with you, is it a sure sign she's willing to kiss you?
After this date, I asked her out again but she made up excuses, so I backed off, not texting her at all until she texted me, and she did asking to go out for a drink after work. Here's where I really screwed up. I tried to tease her some, but since I don't have much practice doing that at all, I think I ended up insulting her. For example, I complimented her nails, she said they were done badly, and I responded "because you did them?" That would be an insult, not a flirty tease, correct? She also jokingly said how she did something dumb because she's blonde and I just smiled and agreed, trying to make it look like I'm not serious. Lastly, I ended up stroking her hair saying how soft it was and, immediately after this, she said she had to get going because she knew I wanted to kiss her. We were in her car at work (LOL terrible idea of mine). Before she left, she said she hopes she just doesn't annoy me at work and I responded "you just get in my way sometimes, but I don't mean that in a bad way. you can't help it." She smiled and said thanks then bye.
So, after all of this, I'm pretty sure I shot myself in the foot or, even worse, took the attraction switch and broke it right off with no chance of switching it back on, if it ever was on in the first place. The awkward part about this is that we work together still and I'm shy at work in front of all my co-workers, so I don't really talk to her much. I don't know, I think I not only scared her away, but I think she thinks I'm a really mean person, and probably desperate too. What do you think? What should I do and is there any chance of attracting her after this? (I know I sound like a wuss, but I'm really just shy and working to overcome this. I really do want to talk to her more at work, but it's tough with co-workers around who I don't know well. I feel like I have to talk to them to get to her because we all work in close proximity in a restaurant, and we work in separate areas. I'm in the back and she's in the front)