Even I find it strange that an Adam Sandler movie made it into my top 10, but in the 8 years since I first saw it on DVD, I've probably seen all or part of it more than 50 times. It's one I've taken on trips that almost always gets watched. The concept of this movie really shouldn't work - a womanizing veterinarian in Hawaii falls for a woman with no short term memory. But somehow it's sweet that he has to make her fall in love with him every day.
Henry Roth (Adam Sandler) loves to hit on tourists - he lies to get them into bed, and since they're on vacation they're into it too. He has big plans to do actual research on walruses some day, but in the meantime works at a local aquarium and spends time with his friend Ula (Rob Schneider). One day he goes to a diner for breakfast and meets Lucy (Drew Barrymore) a hippie art teacher having breakfast and they really hit it off. He returns the next day to see her, but she has no idea who he is. The owner of the diner Sue (Amy Hill) explains that she was in a car accident a year ago and has no short term memory and just does the same thing every day. Henry follows her home one day and meets her brother Doug (Sean Astin) and Dad (Blake Clark) who have helped keep the masquerade going every day because they don't know what else to do. Henry spends days and days trying to recreate that magic from the first day - just going to show that timing is everything and he falls in love with her even if she still doesn't know who he is. Henry decides to try making a video and stop lying to Lucy, and over time some things start to stick in her brain, but she decides she's holding everyone back and goes to live in a rehab center. There is definitely a happy, if imperfect, ending, but I won't spoil it.
One of best things about this movie is that we don't have to see Lucy regain her memory for it to be a happy ending. Making the best of a situation and letting good enough be enough sometimes makes reality happen. The whole Adam Sandler crew makes an appearance, as Lucy's former friends and staff at the rehab center. The supporting cast a whole does a good job of carrying the story - particularly Sean Astin as Lucy's body-building brother, Doug, who got outed for steroid use and speaks with a lisp, and Henry's assistant Alexa (Lusia Stus) who is a hysterically androgynous person who eventually hits on Doug. The chemistry between Henry and Lucy is the other big part that makes this movie work - they've come a long way since The Wedding Singer and that chemistry translates to the screen.
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