Tawny Kitaen's character says at the beginning of the film that she'll worry about something "after [her] nervous breakdown." If you know anything about what happened to her in the years since this film was made...
Rick's comparison of Nick the Dick's manhood to the World Trade Center.
Hilarious in Hindsight: In the mind of Tawny Kitaen, anyway. In the scene where Debbie and Rick were playing tennis with Debbie's parents, Rick wails a return over a chain link fence and then yells "Cleveland wins the pennant!" Tawny later married MLB pitcher Chuck Finley and remarked that she found it funny that Finley pitched for the Indians when they won the pennant. Except in Finley's three seasons with the team, they never advanced further than the American League Divisional Series.
Cole crosses it when he tries to take Rick out with a crossbow.
Debbie's father views Rick watching a donkey show during his party as this In-Universe.
Values Dissonance: The joke that Gary has sex with a transgender woman is pretty cringey. Even though the woman is happy and Gary falls in love with her, he's horrified when he discovers her biological sex. Today, the joke may well have ended with Gary actually marrying her and being happy.
