<Ul> <Li> Adam Sandler as Henry Roth, a marine veterinarian with a talent for wooing women and a fear of commitment </Li> <Li> Drew Barrymore as Lucy Whitmore, Henry's love interest with short - term memory loss </Li> <Li> Rob Schneider as Ula, Henry's marijuana - smoking, native Hawaiian assistant and best friend; he is unhappily married to an overweight native woman and has five young, athletically talented children </Li> <Li> Sean Astin as Doug Whitmore, Lucy's older brother, a lisping, steroid - dependent bodybuilder </Li> <Li> Blake Clark as Marlin Whitmore, Lucy's widowed father, a professional fisherman </Li> <Li> Lusia Strus as Alexa, Henry's ambiguously gendered assistant </Li> <Li> Dan Aykroyd as Dr. Joseph Keats, a physician specializing in brain disorders </Li> <Li> Amy Hill as Sue, the Hukilau café manager and friend of Lucy and her late mother </Li> <Li> Pomaika'i Brown as Nick, the Hukilau café chef . </Li> <Li> Allen Covert as Ten - Second Tom, a hospital patient with severe memory impairment (reprised as 220 Tom in Blended) </Li> <Li> Missi Pyle as Noreen, a tax attorney Henry meets at a bar but then tries to fix up with Alexa </Li> <Li> Maya Rudolph as Stacy, pregnant friend of Lucy's at beach party </Li> <Li> Kevin James as Factory worker </Li> <Li> Lynn Collins as Linda </Li> <Li> Joshua Seth (uncredited) as a painter </Li> <Li> Greg Cipes (uncredited) as a painter </Li> <Li> Dee Bradley Baker (uncredited) as a man at the restaurant </Li> <Li> Scott Menville (uncredited) as a man at the restaurant </Li> <Li> Jessica DiCicco (uncredited) as a teenager at the zoo </Li> </Ul> <Li> Adam Sandler as Henry Roth, a marine veterinarian with a talent for wooing women and a fear of commitment </Li> <Li> Drew Barrymore as Lucy Whitmore, Henry's love interest with short - term memory loss </Li> <Li> Rob Schneider as Ula, Henry's marijuana - smoking, native Hawaiian assistant and best friend; he is unhappily married to an overweight native woman and has five young, athletically talented children </Li>

Who plays the daughter in 50 first dates