On a first date?! That would be the last for me. Besides, if he wouldve asked me if its alright to take a train on Motzei Shabbos (on a first date) the answer would have been an unequivocal NO!
Heres my issues:
A- The guy is responsible for the girls safety, whilst he cant ensure that he wont get in to a car crash going on the train on Saturday night at 12 am doesnt seem all that responsible.
B- If this is what he calls putting his best foot forward, I’m scared to think about the alternative.
C- SCOPE OUT THE VENUE. Laziness.