20 Dates

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. In real life, Elisabeth and Myles were married in 2000 and had a daughter but were divorced around 2015, with her meeting and marrying someone else. In addition, a 2014 article by Elisabeth about ending her marriage to Myles states that she and Berkowitz were together for "18 years" and married for 14; if this is accurate, then the film isn't even a partial documentary but 100% fiction and that all of the drama in it was fraudulent.

Synopsis from Wikipedia, CC BY-SA 4.0. Everything below written here.

Poster © the film's rights holders.