(Question) What do you call 100 film critics buried up to their necks in sand? (Answer) A good start. Well, I don't know Peter Mattei from Adam but if he is the budding auteur his filmography suggests, "Love in the Time of Money" is a "good start". A classy shoot with whimsical music box style music, this flick looks at a chain of tenuous relationships as it moves from person A to person B to person C...etc...and back again ending with persons A & B in carousel fashion. The film gently probes the unhappy circumstances of nine people with finely rendered shadings beginning and ending with a street whore and her client. The downside of this film is the lack of a story which may have something to do with the many critical slams it received. I watched the behemoth "Angels in America" last night and was bored at the end while this little concatenation of character studies kept me spell bound. Use caution. I may be the only person who really liked this flick. (B)

....ripoff of a dozen better films. Particularly Steven Martin's "LA Story", which at least had the grace to be obviously fictional even though it starred his then-girlfriend playing his girlfriend in the film.
Yes, naive boys and girls, "20 Dates" IS a mockumentary, although I am not absolutely certain that was Myles Berkowitz's intent when he started. My impression is that he started the project semi-seriously, then quickly realized that it would be pathetic and not funny unless he made the situations more and more ridiculous. As a result, the whole thing has an uneasy, cheap and insincere feeling about it.
As someone smartly pointed out, the film has two of the "dates" suing and putting restraining orders on Myles and yet they appear in the film, which would be impossible as it would require a consent form. It also appears to me that the majority of women who appear as "the dates" are professional actresses (albiet not famous ones, excepting Tina Carrere) -- they are simply too obviously pretty, polished, thin and comfortable in front of the camera to be average civilians.
Mr. Berkowitz makes a classic error in only casting this kind of very pretty thin actress, instead of utilizing a variety of believable women, which might have made the premise (even in a mockumentary) more believable and funnier. He also skates over what is probably his real-world problem, and which is that both the movie character and the real world Myles Berkowitz appear to be functionally unemployed (his real life IMDb credits are practically non-existent, excepting this film). Even in the world of the movie, his ex-wife divorced him for never being employed. I think the viewer (let alone Mr. Berkowitz's real life dates) are deserving of an explanation of he manages to live in one of the most expensive urban environments in the US, in a luxury apartment, driving a fancy car and eating out at pricey restaurants when he doesn't seen to have any source of income whatsoever. (Is he drug dealer? Living off his rich parents? No clue!)
You can get away with most anything in a film, if the jokes are really funny. "20 Dates" is painfully, embarrassingly UN-funny. Mr. Berkowitz's idea of a joke is to have his character, while on restaurant dates, announce to his companions how the food served is likely to give him either diarrhea or constipation -- the WORST kind of childish potty humor.
It is not very surprising to discover that Mr. Berkowitz never made a film before "20 Dates" and in the last 8 years, has not made a single film, appeared as an actor in anyone else's film OR had a writing or producing credit of any kind. My gut instinct tells me that this film was not financed by "Elie" (the gangster money man who appears off-camera) but more likely by Mr. Berkowitz's affluent parents, or perhaps represents a shocking abuse of credit cards. Whichever it was, we can all rest easy that we are unlikely to have to see Myles Berkowitz or any of his creative efforts EVER AGAIN. Hallelujah!!!