He: ((This "playing dumb" act isn't getting me anywhere! Why can't I just come up with the courage to just ask her out? Grrrrr.))

I think its critical to the object of affection to at least know your in the same room when you order them a Cafe Ole. Otherwise how else would they know you were stalking them in the first place. P.S. A nice little note with a smiley face on it might be the way to go, even when you dont want them to leave. On the other hand, ask her if she would kindly bear your children because you noticed she has worthy hips. ;+

Do men really play dumb?  Not in my experience.  I think they are more likely to act like they know about something (even if perhaps sometimes they don't) or to pay attention to us or do or say things to try and make us laugh before they ask us out.  I would say because if we respond more positively then they think we would be more likely to go out with them.  Usually just an invitation out of the blue we are less receptive to because although we know where it is coming from we have not thought about that person at all.  Of course that causes us to think about them so though we may not be so receptive at first if he keeps on then eventually we start thinking of ourselves with him so we become naturally more receptive over time as long as he remains interested but polite and does not push it too hard. 

You mean the dumb thing is an act?  Seriously?  I never knew that; it seems so real...............

i would just come right out and ask her