I moved into a flat with four other people last year and made an instant connection with one of my female roommates. I asked her out twice over the following month but she said no both times, so I took it as a pretty clear sign and never brought it up again after that.
Everyone else eventually moved out, leaving the two of us alone in a big flat. We developed an excellent and extremely close friendship (even if she wasn't attracted to me, I still really liked her), told each other everything and were literally always together.
Nearly two years later, the time I asked her out is ancient history but we still live together and are still inseparable. We go out together and get hammered one night, then once we get back home, we're both out of it and start getting all deep and soppy. I end up telling her that even although she turned me down when we first met, I'd always had feelings for her and loved her very much. She just starts crying and leaves without a word.
A few weeks later we come home drunk again, only this time she's the one who drunkenly opens up. What she said next hit me like a punch in the chest. As it turns out, she'd been attracted to me right from the start and also wished we were more than friends, she just never had the confidence to say.
You see, I had recently broken up with my girlfriend when we met, so when I asked her out those times she thought it was just a rebound and said no. Of course, I thought she just meant no and never asked again, which only served to confirm her suspicion that it wasn't genuine.
Where it gets complicated is that she says she doesn't remember these conversations and I'm not sure of whether they were just drunken nonsense or a sober person's real thoughts spilling out. I've tried talking to her, but she's very secretive, hates serious conversations and will do almost anything to avoid one.
The thing that bothers me the most about all this is that we live together. This is her home, where she's supposed to be able to come to get away from the stresses of daily life, I don't want to be dropping more problems on her, she's got enough going on as it is. I care about her a great deal and her happiness and well-being is very important to me, but all I can think is 'What if it would work...and I don't take my shot?'