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Well, after one post of help, which actually helped quite a bit, and reading other threads I've somehow managed to eek it out. That is, the first date. Original thread: http://www.loveshack.org/forums/transitioning/friends-lovers/496182-love-my-room-mate"

 

I know this kind of belongs in transitioning, but I'd really like to get as much visibility and input as possible. I'm an utter ball of nerves about this, which is a rather new experience.

 

My best friend, and room mate, whom I've been absolutely crazy about has agreed to go on a real date with me. I mention real, because in reality we've been 'dating' for months. Doing the whole thing minus actually calling it that.

 

Within the recent week, she became distant in mind as well as body. She was...flustered I would say. It came out that one of her friends liked me, and that another guy at work liked my room-mate, and her friend was going to ask me on a date. That night she seemed almost upset, she was hanging out in the kitchen with me, and she suddenly decided to change her shirt behind me as I was making dinner, as I spun to grab a different spatula she was standing there shirtless but back turned, and I kind of got startled. She noticed and asked "So...do you want to see?" And well, yeah. So that happened. This came straight out of the blue.

 

The next day she (my room mate) asked if I had told her friend that there was no chance. I told her that the friend, who approached me said "You know, if I was ready to date I would so ask you out." I responded kindly but without an answer to the hypothetical question. So, then my room mate said, on the way home after picking her up from work "Well, you gotta give people a chance you know? Don't follow my example." I just laughed and then she said "Well...if you agree to say yes if she were to ever ask you out, I will go on a date with you. Even if she never does ask."

 

She later texted me saying she was sorry if it was awkward and that she just wanted to know that she at least gave me a chance so that possibly she could have a chance to pursue other interests.

 

So to my questions;

 

1. This seems too good to be true, or perhaps I had followed the advice too closely and pushed any chance with her out of my mind so it is just coming as a shock to me.

 

2. Is she trying to find a get out of guilt jail card?

 

3. Holy hell, how do I plan a date with someone I already know so well?! I'm thinking of doing a scavenger hunt with areas and things relating to how we got to know each other and stuff we've shared leading up to the main date. Which of course I know I have to take charge, as she has said she likes guys to do, and cross that friendship/possible-partner line with flirty physical contact. I've never been in this type of dating scenario before, it's always been rather text book with other women.

 

Any help would be great. I need to knock this out of the park. Pining after her for a year now and here's what I think is the only and final chance.

 

P.S. Sorry for the rambling structure of the post.

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