At one point Arthur requests that they stop off at "Dairy Queen for a small cone." There are not now, nor were there ever, any Dairy Queens in the New York City area. As of this date (4-12-13) there are 2 planned Dairy Queens opening soon in Massapequa, NY (Long Island) and Staten Island, NY. If you wanted a Dairy Queen cone back in 1998, you'd have to travel to New Jersey or Upstate New York.
Doug and Deacon pay a man to streak naked along the crowded city sidewalk. However, the man's yellow-colored underwear are briefly visible as he is supposedly running naked through the scene. This occurs at 10:18 minutes into the episode, and the underwear are visible on the actor's left hand side (the right hand side of the screen), just above the orange and white striped construction barrier.
The biggest fear that Doug has is running into Carrie, yet he drives the rental car right near Carrie's office building.
Doug and Deacon are watching a big fight on TV and win $5000. Doug suggests they blow all the money tomorrow. Deacon asks "Can we do it Wednesday, I have a dentist appointment tomorrow." That would mean they were watching the fight on a Monday night. Big fights take place on Saturday nights.
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