bjjkid, are you referring to extravaganzas involving other people, and making sure it’s all on the camera, etc. for posterity? Or just, as SJS says, having the shadchan do it all?
I think that you underestimate how meaningful a dignified and private proposal can be. Iy”H by you.
As far as privacy, I think it’s fine for the shadchan to be involved to the extent of there being someone for the boy to ask, if I would ask her now would she freak out?
And – call me goyish – but I think the boy should ask the parents’ permission, even though if they’re going out that long, duh, it’s understood that he could ask at any point.