For those that read this and reply, thanks.
I know this is a extremely long post, but I feel that I need to start from the beginning to set up the mood so it doesn't seem like scheming or anything like that. And please don't think I'm trying to justify anything, I'm merely stating things as they are. I broke it into chunks so it would be easier to read.
My older brother is 27. He dropped out of high school then got his ged in adult school. He's "punk" and is in a pretty horrible band. He smokes weed every night, still lives at home. Never went to college. Worked at a coffee shop (at the time) and is now a waiter. He complains that my mother favors me and doesn't give him independence yet still lives at home. I automatically love him because he is my brother, however as a person I think he is pretty lame, lazy and mean.
July 2004
My 21st birthday. The day before I move to LA my older brother brings home this girl named Destinee (above). Realizing it was my 21st birthday, she took me and Carter to Friday's where she used to bartend. She proceeded to get me drunk (at 2pm nonetheless).
I really didn't think about this until now, as I recollect, but the next morning as I was getting my stuff together to leave to the airport she gives me a call asking if I wanted to have breakfast with her. But I couldn't because my flight was early. I didn't think about it, but now it does seem a little weird that she called me for a one on one breakfast and not invite my brother.
That summerWhile I was wasting my life away in LA at stupid Hollywood parties, Destinee would call me every once in a while and complain about my brother. So through this we basically became friends.
Around late August, my other brother was diagnosed with Cancer (He's cancer free now). So I decide to move back to northern california.
To summarize, me and her become good friends as her and my brothers screwed up relationship falls apart after a few months of dating. She catches him seeing his ex-gf, she finds an email he sent to some girl saying he is in a "tour punk band and has always fantasized about making love to a girl like her" and basically he lied non-stop. He also threatened to kill himself because she wouldn't take him back. (which she didn't, however it such a horrible thing for him to say because he knew one of her ex boyfriends did infact kill himself because they broke up)
Sept 04-June 05They break up. I get accepted to Central St Martins and Parsons. I intially plan to go to CSM in London but due to money costs (non of my scholarships and grants were valid overseas) I decide on parsons fall 05.
I start working at a mag in san francisco again, she has a job at a law firm in san fran. We meet up for lunch a lot. Become super close. I start to like her because we're so similar. Same age, both vegetarians, into fashion and art, 80s new wave. Everything. However she dated my brother so I set all that aside and besides I'm moving to NYC.
She starts seeing this guy named Erick, I actually know him through people. So basically I focus on working and getting ready for NYC.
Between then and me moving to NYC in June, I am stil the go to guy for problems (aka I'm in the friend zone I think). I help them resolve stuff and their relationship goes steady.
June 05
Me getting wasted with her the week before I leave
I move to NYC. She calls every so often about problems with the boyfriend, I give her advice. Same stuff.
August 05I start dating Amanda.
Sept 05 - NowDestinee calls me again every so often about Erick. They break up about a dozen or so times and get back together again just as much.
She texts me, IMs me, leaves me voices mails or calls, and each time she starts telling me how much she misses me (this could be just a friend thing), and that she loves me (this is a little strange to me). However, I start to tell her the same things..but then saying I love you to her made me feel uncomfortable because it was something I wanted to steer away from, so I turn it into a joke (I start saying NUBS instead of love) She plays along, but still says she loves me and misses me a lot.
I surpress it because I was dating amanda. She was dating erick. I'm in NYC. She dated my brother.
So, a while ago, Amanda breaks up with me. Dess finally officially breaks up with Erick. Since then, she's been telling me she wants to come visit. That she wants to go somewhere on vacation with me (we decided to go to Hawaii this summer). That she wants to move to NYC and just get out of California (She's a makeup artist). She still tells me she misses me. She has been lately telling me that she's been having Peter withdrawls and that whenever she eats certain vegetarian foods it reminds her of me.
Earlier, I told her that my last semester history teacher died. She was pregnant and had a stroke. She gave birth to her baby prematurely (7 weeks) and then slipped into a coma and passed away Wednesday. It was depressing and shocking. I still can't believe it.
Destinee commented that its scary to think we could die any minute.
I took that as a cue, and I started to say "Destinee, you know what. I..."
Then she says "I have to go to work..wait WHAT! WHAT"
Then I said.."YO FACE THAT'S WHAT" (Inside joke

)
and then she goes ok! talk to you later.
and that was that. So, I was about this - - close to talking to her about it.
After this story..the big question(s) is (are)
1. Am I being paranoid..or does it seem like she likes me as well but doesn't want to say anything?
2. If something were to happen between me and her, would it be shady? I am not close with my brother at all and he is bitter at me for being friends with her but doesn't express it.
The kicker to this story is that my brothers ex gf (who he met up with when he was with destinee) has gotten back together with him. She's actually considering moving to NYC to go to Parsons (she graduated from UC berkeley). Being the leech my brother is, he coincidentally decides to go to the NY Film Academy. My mother tells me that he made her deposit tuition for it already. However, I made it a point to my mother that he is not living with me. However also I would like to point out that my brother is one of those types that talks rather than does. Before this he was supposed to study to be a music teacher at UCSB, before that, a park ranger (WTF?), before that? a cop, before that a bartender..you get the picture.
So to make this situation even stickier, if this is the one time he actually follows through with what he says, he could be living in NYC as well. I know, NYC is big, but if he's following his current GF, that means she will be in the same fashion building as me which means there might be a chance he will be around me and Destinee, this is assuming that something developes between me and her (and yes, I would let her move in with me)
I don't know if this matters or not (I think it does) but she didn't sleep with my brother while they were dating either. To add another R.kelly twist to this story, there is speculation that my brother is actually gay, but does not want to admit it. This is not a joke kind of thing, but pretty serious.
He got upset at Destinee for trying to, and a direct quote from her, "Take away his virginity"
He admits to me and my best friend Troy (who is his friend and a friend of the family for years) that his current gf (who he's dated now for a total of 5 years) that they never had sex either and he's only fingered her. Which makes me believe he's a virgin, which is strange because he used to come home bragging about all the girls he's i can't readed and he also told me him, destinee and her friend had a threesome.
When me and troy used to have AOL, we would find pictures of naked men on my computer after my brother would use it. When we asked him what was going on he replied that he was pretending to be a girl to see if they would send pictures.
He has a gay friend named Ali who he would have crying arguments with over the phone.
A gay porn catalog was shipped to my address here in NYC. After some credit checking, I find that someone had used to card to purchase an online subscription to a gay porn site in California, ordering some items. However, they did not change the shipping address for the catalog and the catalog was shipped to the credit cards billing address, which I had changed to NYC.
He has been rebellious and angry for a long time. My friend and I think he hides under this tough "punk" exterior. We come from a middleclass, fairly well off family, there really is no reason for him to be this way.
So basically, thoughts? if i were to tell her and something were to develop, I would want to talk to him about it..but in all honesty should I bother?