My Date with Drew (2005)

"Life is a gamble, but without risk, there's no reward." - Drew Barrymore. These words have resonated with Brian Herzlinger since his childhood, when he first laid eyes on the enchanting Drew Barrymore in E.T. The Extraterrestrial. Fast forward twenty years, Brian, now a penniless 27-year-old aspiring filmmaker, embarks on a daring journey to win a date with his lifelong crush. The catch? She is the radiant and unreachable Drew Barrymore, while he's just Brian, a dreamer from New Jersey. Undeterred by the odds stacked against him, Brian rallies his film school comrades, armed with a borrowed video camera, due back to Circuit City in a month, and the $1,100 he fortuitously won on a game show. The winning answer? “Drew Barrymore”, a prophecy that fuels their audacious quest. With a ticking clock and a dream that refuses to dim, they set forth on a one-month mission to pierce the star-studded fortress that surrounds Drew Barrymore, hoping to ask her out on a date. My Date with Drew is a heart-warming tale of an ordinary man who dares to chase the extraordinary, despite the seemingly insurmountable hurdles set in his path. A blend of humor and modern-day courtship practices, this award-winning story gives a witty and insightful peek into celebrity culture and the lengths one will go for passion. Brian's journey illuminates the power of dreams, reminding us that sometimes, the biggest risk is not taking one at all.

My Date with Drew is a documentary movie featuring Drew Barrymore and directed by Brett Winn.

My Date with Drew is currently streaming for free (ad-supported) on FILMRISE, Freevee, Kanopy, Redbox, The Roku Channel, Tubi TV and VUDU Free.