* HilariousInHindsight: Henry's first recap video for Lucy claims that the Red Sox have won the World Series since her accident. This is followed by "Just kidding!" The movie came out in 2004, just a few months before the Red Sox won their first World Series of the 21st century.
** Barrymore's next movie, which she produced as well as acted in? ''Film/FeverPitch'', loosely set across the backdrop of the 2004 Red Sox season.
* {{Narm}}: While Lucy's condition is not funny, what caused it... sort of is. "Stray Cow Causes Car Accident". Given the movie's a comedy and the fact this accident happens in Hawaii, while it's more than possible, it can be funny for some viewers.
* NightmareFuel: Lucy marrying Henry and having to remind herself of their marriage, meaning she wakes up knowing she went to bed as a care-free teenager and is now in a marriage with a stranger miles from home, though at least her father is with her at the end. Worse, they have a daughter, so unless they adopted or used a surrogate, she would have woken up pregnant for at least four months straight with the only memories being those from before her accident.
* {{Tearjerker}}: The day where Lucy realizes on her own what has happened to her [[spoiler: and the fact that this is not the first time it's happened]].
** Lucy and Henry tearing up [[spoiler: Lucy's scrapbook so she'll have no memories of being with him.]]
* TheyWastedAPerfectlyGoodPlot: Some critics complained that the movie didn't live up to the promise of re-teaming Sandler and Barrymore after [[Film/TheWeddingSinger their more familiar collaboration]].
* TheWoobie: Lucy.
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