20 Dates (1998)

20 Dates is a 1998 American mockumentary film. Myles Berkowitz directs and stars as himself, a man who decides to combine "the two biggest failures in my life--professional and personal" by setting out on a filmed quest to have 20 dates and come out with both a movie career and a love interest. While most of his dates are disasters of varying stripes, Myles ultimately meets the lovely Elisabeth on his 17th date and they completely hit it off, leaving him with a new dilemma when he wants to finish the movie anyway and puts his new romance at risk.