When Nicole (Jennifer Aniston) is at the Horse track she is wearing black high heel shoes but when they bump into the SUV that is following them, she steps over Boyd's foot to press the gas pedal and then she is wearing a nude color shoe.
"Cupid's Cabin" is shown to be at Exit 22. If they were traveling back to NY via the Garden State Parkway from Atlantic City, Exit 22 would be 16 miles in the wrong direction (south) as the parkway exits are numbered in ascending order from south to north, and Atlantic City is Exit 38. Also, there is no exit 22 on the Garden State Parkway.
The characters are leaving Monmouth Park Horse track (about 1 hour north of Atlantic City) and headed north back to NYC. In the next scene Milo is tempted to gamble when they are driving in Atlantic City. Atlantic City is the opposite direction from Monmouth than NYC. They would never be near or pass through it.
Where Nicole lights the road flares in the trunk of the car, a New York Route 135 sign is seen. This is the Seaford-Oyster Bay Expressway in Nassau County, NY. It would be quite the trip for Milo to travel from Atlantic City, through New York City, to Long Island. When Nicole needs to be taken to jail in New York City.
When they go to their room in the Borgata, Milo says that she will be paying for it since he lifted her credit card. However all the Atlantic City casinos require picture I.D. before you can get a room. It would have been obvious that the card was not his.