Thanks for the question.

A “proper” date means two of you one on one.  The place doesn’t matter as much as the intentionality of making sure it is just the two of you.

If this keeps happening over and over again, where it is just two of you but feels like a hangout, say…to meet at the coffee shop or for dessert somewhere, simply say (with a smile), “Are you asking me out”?  

He will either say, “yes, I guess so” and laugh with you or try to justify why it is just a hangout.  Force him to say which it is.  You’ll jump high on his respect-o-meter and you’ll force him to step up his manliness, all good things.

On a side note…and now let me get on my soapbox…it is increasingly disturbing to hear about the number weenies my generation has raised (but really this is just a manifestation of the daycare/divorce generation), but I get many, many private messages reinforcing what you are saying.  

There is nothing wrong with hanging out, but when a guy can’t muster the courage to ask you out then I wonder how this will look down the road with kids, bosses, neighbors, etc., etc.  

You can help him man-up to a degree but if I were a young lady, I would look for the Gentleman that understands what I am saying.  Bold but humble.  Confident, not boisterous.  Kind, but would never let anyone trample over them.

- Dad