And, strangely enough, he will win.
Neither railroads nor inland steamship lines are curious about the lady who accompanies you into your berth, compartment or drawing room.
If you pay for and buy your ticket for two, in advance, no questions are asked, nor does the line have authority to eject you if you forgot to buy her a wedding ring.
(INSIDE STUFF: Though Pullman employes may request the lady you met on the train to leave your room, they seldom do.)
(INSIDE STUFF: It is a felony to transport females across state lines for immoral purposes.)
(INSIDE STUFF: Adultery is a felony in New York State. But there hasn't been a prosecution in more than 100 years.)
Experienced travelers carry as little baggage as possible. Furthermore (especially if you're female) you'll want to buy most of your clothes in New York.
Domestic airlines limit you to 40 pounds of luggage per person with a stiff surcharge for extras.
Tipping is not permitted on airlines and your stewardess will be insulted if you offer her one. But you are expected to remunerate the red cap porters who carry your luggage from cab to plane or airport bus.