Ok, to start things off I'd like to thank anyone who reads this and helps out in advance, it is probably going to be a very long post but your help is much appreciated.
Let's start with some background info about myself. To keep myself annonymous, let's call me Matt. I'm a 19 year old college student from NY, who over the years has had numerous issues when it comes to woman (not trying to put myself down but it's true.) Basically I find myself in relationships for a few months and hear the whole "you're a great guy and any girl would be lucky to have you but I'm just not ready for a serious relationship right now." Basically I'm the nice guy and I know it, but avoiding to be the nice guy is unnatural to me and makes me come off as something I'm not. I'd rather just try and be myself.
Anyway, I have had a few relationships that went no where and overall I'm trying to learn from my mistakes, but I keep getting put in situations that make that difficult. Now for my current situation.
To keep things easy to follow, I'll list all the people involved in the story up here, so you as the reader will get a little better of an understanding.
Kim - We'll call her K. She is a really good friend of mine, who I have known since I was a child, who initially was trying to set me up with the HB 10.
Rick - We'll call him R. Rick is Kim's boyfriend. Over the last few years I have become good friends with Rick, and I see both him and Kim nearly everyday (basically I'm a third wheel.)
Stacy - We'll call her S. Stacy is Kim's older sister. It is clear that Stacy has a crush on me, telling me numerous times how into me she is.
Valarie - We'll call her V. Valarie is the HB 10. She was in a very long relationship with her ex-boyfriend, lasting 5 years.
So as I said, initially Kim who works with Valarie, knew that she was my type and tried getting some info as to if she was single. This was months ago, and Valarie was still with her boyfriend at the time, causing me to face the facts and just stick to harmless friendly flirting whenever she was around. I've been around V for a few months now, and she is pretty comfortable around me now, which i'll expand upon in a second.
So from what I've gathered from V over the last few months of knowing her was that her relationship struggled numerous times, always resulting in her getting back with her boyfriend.
Knowing this, when I heard they had broken up again, I assumed it was just another temporary break up and they would end up together again. This time was different however, and you could tell she had no intentions of going back with him.
Now keep in mind, during their relationship I never went out of my way to try and talk to her outside of anytime we were hanging out with K and R. Regardless of the fact that she is the most attractive girl my age I've probably ever seen (not trying to put her on a pedestal, but it's true, all of R and I's friends agree), I've never given her much attention up to this point knowing that she had a boyfriend who she would continue to run back to.
Now towards the end of V's relationship, during the time where we were just friendly flirting, V told S that I seemed like a real genuine guy and eventually we were going to get married. I took this playfully, telling her to dream on, and sometimes playing along with the joke.
This is where things change. The other night, I want to say a week ago, Kim, Rick, Stacy, Valarie and I were at a party at Kim's house. Everything seemed normal, other than the fact that I was about to get some information from Stacy that I didn't see coming. Basically V told K, which spread to S, that she could see herself dating me but not right now because she wasn't ready to date yet coming out of a 5 year relationship. At first I didn't believe it, but later in the night K confirmed it with me (she was actually mad at S for telling me, thinking I would "change" knowing this info.)
Still in disbelief, and slightly drunk, I managed to get V's number in order to talk to her about a day she had asked me to hang out with her, K and some more of her friends and their boyfriends. I gave her my number and told her to text it so I would have hers too.
A day goes by, and I don't text her, seeing as the only point for me to text her would be talk about the next time we would be hanging out. Later that night after not texting her, K tells me that V was asking about why I didn't text her.
Another day goes by, and she texts me, reminding me of the day we were supposed to hang out. This leads to some flirting, and eventually I told her she was cute, and she gave me the same response back. Even though it seemed fine when we were texting, the next day V went to K saying that I was acting weird, and asking her if K told me that V said she could see herself dating me. She denies it, but I get the idea that maybe I need to pump the breaks.
One day I randomly texted her just to see what was up (probably not my best idea after showing enough interest in her to tell her I thought she was cute, but whatever.) We texted throughout the day, and eventually she transitioned into a deep conversation about issues with her family. Taking into the consideration that it seems that a big part of the reason her last relationship failed was due to the fact that her ex-boyfriend never truly cared about what was going on with her, I made sure to try and comfort her and let her know if she ever needed someone to talk to that it was cool if she texted me. (Possibly too friendly?) She responded positively, but I made sure to chill with texting her to make sure I wasn't smothering her and putting her on a pedestal.
So yesterday comes by and we go to a theme park. It was K,R,V and I. Going into this I knew it wasnt going to be a double date, but my goal was to make sure that I could try and make sure things weren't awkward given the fact that I had not hung out with V since her negative response to K after I had called her cute.
Everything went fine, there was some minor escalation that she actually started so there was some very small progress.
She just texted me today, asking if she was going to see me tonight because she was staying at K's for the night. I'm about to go see them after I post this.
Now for my issue. Basically I don't know how to handle this. Regardless of the fact that I am very into V, I don't want her to know that and come on too strong and scare her away knowing she just came out of a long relationship. Its hard for me to get a read on the situation, I feel that there is potential there but I don't know because I can still see that she gets upset about her ex time to time. Right now I just plan on being myself, because that is initially what attracted her to me, but I want to transition my time with her to be one on one rather than in a group every time, without scaring her away.
Thanks again for reading this long post. Any advice toward how to handle this situation would be appreciated.