UPDATE:
We texted a little yesterday, she initiated the convo 2 days ago, I just didn't respond until yesterday.
We spoke on the phone for a little over an hour, it was casual and fun, but she was kinda mean at a few points in the convo, all in all like a 4/10 in terms of how I felt after it was over. Too much talking on the phone. You need face to face time, and what's with this 'kidda mean' comment, be specific, was she playfully teasing, or being disrespectful. It matters....
I did text her afterward and she responded with a a cute smiley face (A specific emoticon she used to use back when we first started talking) I really don't see how this matters.
I'm considering making plans/just randomly bumping into her next week at some point. Thoughts? Make plans, yes, planning to ramdomly blunder into her... very weak. Just call her up on th ephone and ask her out. You are overthinking this. Trust me she will have a lot more respect for you if you just come out and tell her what you want instead of trying to make this look like some kind of accident.
Also I feel I should clarify, I'm not looking to sleep with her, but to try to go for a relationship.
Wrong mindset brother, you are head for the dreaded FZ if you don't pull out. Women have to know that you are interested in fvcking them, otherwise she doesn't know what to do with you. Women flee from guys looking for a relationship, and end up in relationships with guys that start off just wanting to fvck them.
I figure if we hangout next time and I grab her and and she holds back for a while its a positive signal and we can try to move work through this and go forward and I can be more assertive and be like "hey I'd really like to take you out on a date sometime." I really don't understand what you are doing here.... This doesn't make any sense. Figure out something YOU want to do. Rock climbing, kite flying, bowling, whatever it is that you like to do, and intite her to come with you. Settle on a time, place, and activity and tell her what you two will be doing... trying to feel her out to see where you stand makes you look weak.
I'd also like to clarify that while I am excited about this opportunity, I'm keeping myself in check. As in, next time if we hang out and she rejects my attempt at holding her hand I'll just feel embarrassed if anything, I'm not putting my heart out there for her again. I'm still limiting how much I text her and when I even do contact her, and what I say. No more lovey-dovey crap like we started off with back in June cause all that did was hurt me in the end.
If you want to hold her hand, then hold her hand, if she pulls away.... Try this, it works 3 out of 4 times. If you grab her hand and she pulls away tell her, with a smile and a wink, "Hey, I am holding your hand or grabbing your @ss, your choice." Three will laugh and hold your hand, the other will want you to take her home... which is fine. At some point in your interaction with a woman you have to decide when you are willing to either move things forward or burn the bridge.