I recently had the following dilemma. Our family car was not drivable and we needed a car for my date. Would it have been appropriate to have the shadchan ask the girl’s side if we can use her car for the date? Or should I just have spent the money and rented a car? [At that point, we didn’t know how long we’d be car-less.]
While the tendering of such a request certainly carries some risk of resulting in being perceived as one who is a bit off the beaten path, in the grand scheme of things, I do not imagine it to be so recherché an appeal as to be truly out of bounds. And if were a third or fourth date, and good rapport had already been established, it might not even ruffle the most delicate and sensitive of feathers. However, for a first or second date, or even a later date amidst a shidduch that for one reason or another is tenuous in its atmosphere, it would likely be best to err on the side of caution and borrow or rent a car, so as not to unnecessarily weird the other side out, over what is really nothing more than a triviality.
May the Rocheiv Shamayim B’ezrecha see to it that we all get where we need to go smoothly, safely, and securely.