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I dunno, as someone who works behind a counter (diner/restaurant place), I'd think that if a guy customer started off with 'this is kinda weird but...', that would just make it something more to laugh about. Its hard to describe, but at least with a line like that in the front, it lets the girl behind the counter KNOW that you know you're going out on a limb, and its not terribly awkward afterwards. And I dont think that line takes away from the confidence factor at all, because you're asking out this girl you dont really know... thats confidence right there.
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I agree with what she says. I think the "This is weird, but..." line would be endearing and help break the ice a little. Sure girls want confidence, but not to the point of arrogance (which you guys are not careful enough about... Arrogance is a HUGE turn-off). Saying this line will show your human side a bit--it's kind of cute when a guy sees a girl he really likes and gets a little nervous--but at the same time, she's not gonna doubt that you're gutsy if you're asking her out over-the-counter.
Jam it back in, in the dark.
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