When Doug falls down the stairs of the subway station he lands next to a puddle of water. In the next scene the puddle is not there anymore.
When Brian and Bonnie arrive at the exhibition, the movie showing in the cinema is Barfly (1987), when Brian leaves, it's Casablanca (1942).
The length of Brian's hair changes frequently.
When Brian Flanagan takes a picture of Doug Coughlin on his yacht, he is sitting with his legs crossed, later he puts one foot up on the couch. When Brian looks at the picture later, Doug's foot is up on the couch in the picture.
Brian is wearing white shoes in one shot while Jordan was drawing him, in the next shot when he grabs her drawing his shoes are off.
While inside the ambulance in Jamaica, the steering wheel is shown on the left side. Jamaicans drive on the left side of the road thus the steering wheel for vehicles in Jamaica are on the right side.
A server needs a Cuba Libre prepared. Brian later says to her "You bitch! Why didn't you just tell me that it was a rum and Coke?!" The drink also contains lime juice. (Both his recipe book and the Server are wrong.)
Whilst at Flanagan's place after a drunken night, they are watching a live broadcast boxing match featuring George Foreman vs Ken Norton. Since the film was set in present day US (1988) and the boxing match took place in 1973.
Crew members sometimes visible in the reflections of the actors' sunglasses.
While in the nightclub, Jordan tells Kerry that she's known Brian for about 10 hours, yet they actually met the day before.