Your friend only takes one train. He'll get off the last stop which is NY Penn Station. He can either buy the ticket from the sales agent at the station (if there is one) or he can buy the ticket from the machine which is at every station. If he chooses to buy his ticket on the train itself, he can do that also, but, they charge I think something like $5.00 extra. The trains usually run on or close to schedule, so if he takes the 5:07 and even if there is a slight delay he will be able to get uptown in time. When he gets off the train at Penn Station, they have a cab line right in front or take the subway which is right there also, on the corner. He can even buy his ticket in advance. I do that for my dd when she takes the train in. This way if she's running late, she already has her ticket in hand and just has to board the train. Hope this helps....