Sounds like you've dated some real assholes and that makes sense because it's the real assholes that always make the first move, they just throw a bunch of shit up against the wall until something sticks.

That said, it's a cool and classy move and I would be thrilled if a girl said that to me, but it does take a little courage to pull it off.

You have a few things going for you... 1) you said you got a flirty vibe from the guy 2) you are hot as fuck so your chances are very good that he will respond 3) you have nothing to lose and everything to gain.

If doing the same things hasn't worked out for you, then trying a new approach is a logical option.