We're Great Friends, How do We Date?

Visitor's Question from a 21-30 year old Male
There is a girl who I have known for a few years now. She used to be a roomate of one of my best friends. I saw her every week or so but never really did anything with her directly.

A one thing to note here is I have never really been good with women. I always move into a relationship or dating situation and come out as a friend. This is largely because I often dont have the confidence (fear or rejection) to establish that I would like to take a girl out, over asking them to hang out. I get down on myself because every female I know seems to tell me they think Im a great guy but I can never seem to pin down a relationship.

Back to my original thoughts. I ran into this girl again about 3 months back. I asked if I could have her phone number so I call her and get to gether with her. I got her number. (just got interrupted by a call from her..back to story lol) The next day I went with a friend to a weekend camping/music festival. She was there! She basically grabbed me to follow her with everything she did, whether it was going to see a band or get another beer.
We hung out all weekend and had a blast. I called her the following day just saying I had to much fun with her to not rehash the weekend with her, knowing we were both tired, went to have a drink with her, friends showed up, didnt get a chance to ask her out, sorta a good thing.

I went out to eat (friend setting) with her and we ended up talking about relationships. Explained a situation I had just had a few weeks back about misreading somebodies intentions and she told me that she sorta had a boyfriend but sho she hadn't spoke to in a month, even when he left a message on his birthday. She went into detail about she isnt sure why she hasnt talked to him cause they have always been good friends.

For the next few weeks I spent every available moment with this girl. She would call me every day after work to go swimming or out to eat or what ever. In more ways I started to have romatic thoughts for her but held them back(boyfriend in limbo, i dont want to put any pressure on her).

On a side note I have been depressed on some levels. I get stressed easily. Nothing to serious, im just a really happy person and lately things have been strange because of my insomnia. Just finished school, cant find a job, single yadda yadda. I had been in such a good mood because each day i would look forward to seeing her, and each day she would call me to go do something.

One morning I was really stressed out because I hadn't slept for 2 days, I had just had a conversation with a sorta ex girlfriend I talk about my problems with. She was saying that it might not be such a good idea that I was spending all this time with this girl and not expressing more interest(that she might just be waiting). But i hadnt done this in some ways because she sorta had a boyfriend. I ended up calling her and doing the strangest thing I have ever done. She totally knows how I get when I havent slept, thank god. I basically told her how my friend Sarah got me all worked up over our situation and I had to call her to get it off my chest. Basically I said that I would like to ask her out, but because of stuff in my life, and stuff in hers that she told me about that I hadn't. I told her I would like to ask her out, but nows not a good time. I sorta asked if she would mind if I did in the future, or if that would make our friendship strange. She basically said she didnt think she would mind but now wasnt a good time. I expressed me agreement. Slept like a rock for the first time in days, and went to lunch with her hours later.

She told me that she was going home for the 4th of july to see her friends and family. The only thing she wanst looking forward too was finding out about her bf/gf situation with the kid she hadnt talked to in over a month.
She knows I would do anything for her (sometimes I think this bugs her a little). I even ended up giving her the 4 hour ride to her parents when her car broke down, she called me right away and I went into action.

She was gone for a week. The longest week of my life lol. I was really restless because I went from doing stuff with her every day (road trips to concerts, camping, adventure!) to having nothing to do. In a lot of ways I spent so much time with her I neglected my other friends but they still got a kick out of it because they all thought that we were kinda dating.

Each night she called me with updates of what was going on, and how she wasn't comming home till the next day. The night before she was gonna come home I of course couldn't sleep. I was so excited that I was going to see her again. I was lying awake at 3 in the morning when my phone rang. It was her, it sucked. She was drunk and pooring out her heart. She basically found out that her ex had a new girlfriend, but that she sorta knew that from the start. She in a way was really happy for him because they were such good friends. She went on about how she is so bad with guys, how she pushes them away. She expressed how she was stranded up there and just wanted to be back in town with me (I have no context for this, me as just a friend, or with me now that her other thoughts had come true). I just listened and tried to comfort her.

She got back into town and we went with our usual routines of spending all our time together. Another month or so went by like this and I started to get a hankering to ask her out. One day when I was in a particularly good mood about how a job interview had went I just sorta blurted out that I wanted to celebrate and would love to take her out on a dinner date (doh). We were out at the bar the night before and she just reponded that she was to hung over to do anything that night. I just said ok. I have no idea if that means she wouldn't want to go out at all or just didnt want to that night. She is sorta the kind of person who will just state a direct opinion on a situation truthfully, and you can only take it at face value.

There are so many angles to my situation (at least I think so right lol). Another thing that has been bugging me. When we first started doing stuff I would flirt with her here and there with some success. Im not a very flirty person. With all the women I have dated I am very reluctant with physical contact, often until after the first kiss. Here I know the person is truely comfortable around me. Then its no big deal.

With this girl this hesitation seems to be worse for me because I have a friend who is very touchy feely with everyone he knows. A few times early on when we were all hanging out together he would come up to try to give her a back rub or just pet her arm, stuff like that. This would piss her off royally. She would express this to me, saying she didnt understand why he couldnt take a hint (I know at the same time that it is just the way this other guy is so its always an issue). The problem with this is this makes me even more apprehensive around her. I realized this the other day when we where watching a movie and I had to wake her up because she fell asleep next to me. I sat there trying to figure out how to wake her up, put my arm around her and give her a little shake? poke to the ribs?

So as it sits now we are basically best friends. She told me weeks ago that she wouldn't mind if I asked her out. I sorta did, didnt really get an answer, but our friendship didnt miss a heartbeat. I want to try to flirt with her a little more, but the more time that passes and I notice my reluctance around her, the worse it gets. She calls me all the time (2 times during my writing of this email) even if she isnt really gonna make herself available to do something. "What are you doing?", me: Nothing, you wanna get together? "Im not sure, I might just take a nap." Ok. Call me when your awake. "ok". I dont have many female friends that I interact with on a daily basis. It makes it hard for me to read people(or I dont trust myself because i think ill mess it up). Any advice in this specific situation would be great.

Im sorry for all the rambling. Im an incredibly detailed person and even when I read this I feel I have left so much out. Everybodies life is a drama right lol. Either way its a good vent before I go see her. I care about her so much as a friend, I dont want to mess up our relationship but I have so much regret with the opportunities presented to me. The other thing is she can see something is bothering me when Im around her, and she is always trying to get me to talk about whats on my mind. But how can I do that when it involes her! lol

RomanceClass.com Advice
It sounds like you guys are on a great path! You worked on the friendship part first, the boyfriend issue resolved itself, you spend time together and really get along. The only sticking point now is that you want to somehow LEAP from 'we are great friends' to 'we are dating' in one giant step, and keep getting stuck there!

Instead of leaping, why not just DO it. Instead of saying vague things like "Maybe we can date sometime" say "let's go to see Matrix 3 on Saturday". And then take her out to a romantic dinner beforehand. Buy her flowers for a special occasion. See romantic movies with her. There's no reason to announce every step you take. You guys are already spending the time together. Just change the NATURE of the time you spend together. I have advice here -

http://www.romanceclass.com/miscr/howto/friendlover.asp

good luck!

-- from Jenn
One of Your Friendly Advisors at RomanceClass.com

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