Ok, so a couple months after finishing high school, I notice a girl, who was always pretty quiet and I'm not sure I ever spoke to her in school, had gotten rather attractive. I always remember thinking she was nice, but we just didn't run in the same groups, so we'd never talked.
Cool as a cucumber I send her a facebook message saying how great she is and ask her out. Safe to say that didn't go down so well haha. I ended up explaining the situation to her, we talked it out, and it's fine - she's a bartender at our local pub these days, and we talk a bit if I see her.
That part could probably belong in the "Awkward Flirting Stories" thread haha.
The reason that I'm here is because almost the exact same situation is happening now (I'm now 3yrs removed from High School). It appears I may have hung out with the wrong group in high school haha, this one was well more suited to me. Anyway I played this one a little safer - I did basically start talking to her out of nowhere, but she responded, we've just been nicely talking about work, tv etc.. all the usual things. I haven't got any sign from her that she's necessarily "keen", but it's all been friendly enough. Now 21yr old me has learned, and I can't just go asking her out now, given we've never actually hung out haha. So what's my next step? My best guess is to find out where she's headed one night, do the old "Oh no way, me too" happen to run into her there and talk for a bit there and see how it goes. Thoughts? Or better ideas haha?