I have a friend that I met off of myspace in the winter of 2005. She is originally from the Boston-area, same as me. Both huge fans of the Red Sox, lots of common interests, etc. She found me on myspace because she was moving in to the area and noticed I was wearing a Red Sox hat in my default picture.

As the months went on we shared a night of passion. We watched Nip/Tuck, cuddled on her couch, made out, did some gropping, but then she cut me off, saying she didnt believe in having sex with someone she wasn't dating. At the time I was seeing about 3 girls at once, and I was in no way, shape, or form looking for a relationship, so I let her know that wasn't a possibility (this was in mid-2006). Since then we just decided to be friends, since I wouldn't give her what she wanted. Since then, both of us have been in relationships at the same time.

Fast forward to the summer of 2008. She was single, and I had JUST become single. Being single at the same time, a rareity. We hung out twice, she made lunch for me(IOI??), and we watched tv. We then made plans to go to the bar that night. It was at this point that since we were both single, I was starting to see just how much we had in common, how we are both ambitious, how who knows? We could possibly be a great potential fit! That night we go there, my ex shows up, sees me with this girl (she was always jealous of her), and didnt leave my side, begging me back and ruining my game. Meanwhile, the girl found some guy through a friend, got drunk and they hit it off. Started dating immediately.

This brings us to today. I've lost a lot of weight lately, and she tells me about how good I look, and this/that. She confided in me last weekend that she was sick of her b/f and would soon be breaking up with him. I was shocked because they seemed so happy just weeks before. I hadn't really thought of her in that way since the summer when we were both single at the same time for a day or 2. I had my female friend do some fact finding with her last week and she said that although she is very attracted to me, i'm the only guy friend she has that she deeply connects with, that that likes her for her actual personality, as oppossed to the Double D's the has. So i'm caught in the friend zone, right?

This takes me to last night. I invite her to go watch UFC at a bar. She answers the phone and sounds sick as hell. I invite her out and she said she'd rest up & try to make it (IOI?). She called and let me know that her b/f has to work, but she rested up and said she'd come out for a bit (note, she likes sports, UFC being one, so shes not there just solely for me, she had interest in seeing Chuck Liddel fight). She gets there and i'm half in the bag. I start building kino - little elbow knudges when I make jokes, gently tap her theigh with the backside of my hand to get her attention. My body was sore and I asked her to give me a massage and she did right in the middle of the bar for like 2 minutes. When chuck lost I pretended to be very sad and asked her to hug me. She said as long as I didnt motorboat her I could (we made a joke about me motorboating someone on my 21st bday), and I said that's fine. So she gave me a hug and squeezed deeply.
Interesting thing...any time she would go to the bathroom, or go out to smoke, she would touch my arm or hand (kino/IOI???) to let me know where she was going.

Her roomate locked himself out of the apartment and she had to go let him in. I thought for sure she wouldn't come back, especially since she was sick. BUT, needless to say she came back and offered to drive my buddy and I to her place to crash(we were both wasted). On the ride to her place I asked why she was hesitating to dump her b/f, she said that shes not happy, but hates the whole single thing, hates dating, hates 1st dates, said shes not good at them. I told her an easy way to skip that would be to date me (I said this cuz I was wasted). She was kind of shocked after I said this. She asked "What do you mean?" I said "What do you mean 'what do I mean'? We have a ton in common, we're both attracted to each other" and then my buddy interrupted by puking out the window. It wasnt brought up again.

At her place I made popcorn and she sat on the couch next to me and we watched "you got mail" (this is how wasted I am). Is this an IOI that, with her being sick, and tired, she stayed up another 15-20 minutes to eat popcorn with me and watch this lame movie?

Help me out guys, as of now it feels like I've got one foot in the friendzone, with potential to pull myself fully out once she is officially broken up with this guy.

~Ace

Look dude,,,, forget about the "IOI's" and all the other bullshit. This chick has some interest in you, so just persue her. Forget about strategy and just show her a great time and see what happens.

It just seems to me that you are overthinking it a bit. Forget the friendzone shit and next time you are walking down the block with her put your arm over her shoulder. I say, forget the fucking details and have fun.

Cheers brotha!

***UPDATE****
SO my friend has become single. What do I do? Well, i know that I neg & kino escalate. Be C&F. I know that she is attracted to me, and she does things like calls me after I text her, will meet me if I telll her i'm gonna be somewhere.

Now that she's single, my fear is that she will throw herself on the first dick that comes her way - other than me because she sees me as a "friend." I know she's attracted to me, but I think i might be in the friend zone.

Also, she has re-connected with an old female friend of hers who is single and needy for her time, so, that means she'll be going out more often looking for "guys" since she sees me as just a "friend" im going to have to overcome this obstacle.

As I said prior, it's very RARE for the 2 of us to be single at the same time, so My next couple of moves need to be smart & calculative because who knows if i'll get another chance to convert this friend to a conquest.

If you're reading this I need feedback from each & every one of you. Help!

~Ace