This is going to be long. Preface, I have no game. So I'm working at an event 5-6 years ago, it's a family business. I point out a girl I think is hot to my father while were just bullshitting, turns out its the daughter of one of his friends. There's a short introduction later in the day when my father was talking to her father etc, I was 19 she was 16. I had even less game then, I said hi and returned to my work. After the last day of the event we were working we're packing our stuff up and she and her mother approach, say hello and her mom grabs one of our business cards flips it over and hands her daughter a pen and walks away. Clearly I'm supposed to be asking for her number at this point? I do. Fast forward a couple weeks of random texting and phone calls I had made it really clear that I was into her, she's super shy but admits the same although she has an on and off boyfriend of a couple years and it's a 'bad time'. (I've learned recently that there were SERIOUS family issues at the time, as well as the boyfriend was a complete prick but had her wrapped around his finger) We lived in seperate states so it really wasn't much of an issue anyway as we'd only see each other 5-6 times a year. Fast forward 5 years, I've ended up moving to the same city she lives in for work...and we've become pretty good friends in the meantime. We never really stopped talking...although I've never pushed the issue again. Now that I've lived here a few months though I'm wanting to do so now...we go out for beers/food nearly once a week...I left town for a week and she offered to stay at my place and watch my dog etc. At times I get the vibe that she's into me, but nothing concrete enough to want to jeopardize making things super awkward between her and I if I'm taking things the wrong way. I've been invited to dinner with her parents (again, family friends basically so I know them pretty well) and invited to dinner at the house multiple times, including for easter this weekend. I could go on and on...basically I THINK she's into me, all signs point towards it. She's only slept with that one guy, and told me she's only ever kissed 'less guys than I have fingers on one hand.' Super shy and seems to be pretty naive. I've said some things that I felt opened the door for her to express some sort of interest, but she typically comes back with the 17 year old 'you've got bad taste' or 'you're crazy' deflections. I know I'm being a huge pussy, but I'm going to know this girl for most likely the rest of my life, I don't want to look like a complete creep by coming out blatently and telling her I want to date her. How can I go about this in a manner that wouldn't make things terribly awkward? She's basically my only good friend in town since I'm new to town, and my only social connection at this point. It's seriously to the point where I almost don't want to see her cause I feel like I should be coming onto her...if she was some random chick I just met the door would seem to be wide open, but for some reason I'm having a hell of a time walking through it with this one. Ugh. Questions? Ideas? Want to tell me how much of a pushover I am? Fire away Edit: I'm now 26, she's 22.