20 Dates (1999)

Mockumentary that follows director, Myles Berkowitz, who wants to make a film about his real-life quest to find a girlfriend. Myles somehow convinces a producer with a questionable background, that this venture should be financed. The professionally ambitious, lovelorn director secures a $66,000 budget, starts the cameras rolling, and embarks upon a score of romantic trysts, where he's sure he'll find true love and, simultaneously make a darn good movie, to boot!