Alright guys, so I just made my second approach. This time it was with a cute 22 year old . She was MUCH more friendly and talkative than the previous girl who I attempted to converse with. She was actually a normal non-awkward person. This threw me off because I was expecting a similar awkward conversation as the last approach, but this was not the case.

However, I made the mistake of not making my intentions clear and saying "hey I thought you were cute." or something like that. Instead, I was very ambiguous with my intentions and I stated that my reasoning for approaching her was that I work from home and that I'm just trying to converse with random strangers. Looking back, I feel that this was a bitch move on my part, and I was tucking my balls in between my legs somewhat. Once we had reached the end of our conversation and I had asked for her number, she was somewhat taken aback and simply replied "nooo", in a friendly manner. I looked at her and said "really? Okay, no problem. Have a great day then!" And as I was walking away I could almost see in her eyes that she felt bad for saying no, and perhaps she regretted it, or even perhaps she wanted me to say more to woo her, but I was already on my way off.

Lesson Learned: You have to make it clear that your conveying some type of interest in her personally. Your not just some guy who goes up to people in general and are talkative. There is a reason why you specifically singled her out of the crowd to go up and talk to her.