I'm 19. I asked her out a year ago, shortly after meeting her, but the timing turned out to be awful. She had to leave for uni like a week after our first date. Nothing happened, had a second date, again absolutely nothing happened, mixed IOIs and IODs, everything just felt a little bit cramped by the fact she was days away from leaving for 9 months. We got along really well, just zero sexual escalation from either of us. Not even a kiss.
We're now friendly again. Friendly and mildly flirty. Went to a gig last week with her and 2 guys, had a good time. And towards the end we were playful. Thing was, I was dating someone else at that time (not seriously, met her clubbing, 2 dates, no further than making out) and said as much. I'm now not dating her anymore.
It's a relatively complicated situation, and I've got zilch similar experience to draw from. I was gonna call her tonight and ask her out... again... but it just didn't feel right and I wussed out. I'm thinking of organising a group lunch over the weekend and going full retard with my flirting, then getting her alone to ask her out. Oh, also I've no idea what kind of date it should be. Dates we did last time were picnic and cinema.
Any words of wisdom truly appreciated.