Will Keane (Richard Gere) is a womanizing restaurateur on the cover of a magazine. Charlotte Fielding (Winona Ryder) has her 22th birthday party at his restaurant. She makes weird little hats. Her grandmother (Elaine Stritch) knows him as an old friend of her mom. He starts flirting with her and maneuvers her to a date. After their first night together, he tells her that he can offer her nothing, and she tells him that she has a terminal heart tumor. Meanwhile there is a mystery woman Lisa Tyler (Vera Farmiga) around.

There is a high ick factor especially since the movie hints at him and her mother having a thing in the past. She's playing a giggly little girl. She's literally giggling about him dancing with her mother. He's the weaselly Don Juan type. She's so young that she can't see that he was just trying to seduce her that first time around. She's so clueless that she's shocked by her mother's past with him. It's not romantic. It's just sleazy. Next to Gere, Winona Ryder is like a fawning teenager. And why do they have to keep talking about her mother? I understand that there is a May to December romance that gets turned upside down. It's not as poetic as the movie supposes. The chemistry is all wrong. If she doesn't start off as terminal, then it might make the movie more poetic. The dialog is fairly weak and there is limited tension in the story. I don't know what drives the movie if we rule out happily ever after right off the bat.

"Does anyone still make a hat?" I predicted stage legend Elaine Stritch would say about sweet 22 year old granddaughter Winona Ryder in this variation of the Douglas Sirk tearjerkers of the 1950's and 60's that have been crudely referred to as "chick flicks" over the past few decades. I hate that term because it makes attached men feel obligated that they have to force themselves to sit through in an effort to seem sensitive and romantic. It's a manipulative term that makes me cringe as much as many of the cliches that pop up in them as well as the status symbol it gives women who advertise the private fact that they got their man of the moment or in rare cases their lifetime to watch it with them, often claiming that their man couldn't help but cry as a way of rising above their other gal pals.

It's easy to carp about the age difference between the leads, Winona Ryder and Richard Gere, and yet Gere seems ageless in spite of the snow on his roof. The problem with his character and performance is that he is given a ton of cringe worthy lines that make you laugh out loud at him. However I found myself manipulated by his phony charm and as Ryder's gay friend Simon indicates, he's beyond charming and a perfect catch for any single human. Gere is the proprietor of one of Manhattan's top Soho restaurants where a beet salad actually goes for under $30 (you still wouldn't catch this Manhattan resident in a spot like this) and his efforts to charm the stereotypical temperamental chef are usually successful.

Gere as it turns out knew Ryder's late mother, so he knows grandma Stritch (stealing every moment she's on with her loveable cynicism and wisecracking ways) and conveniently falls for Ryder when he discovers that she is dying of a heart condition. Stritch in her own inimitable way begs Gere (whom she obviously still adores and wishes she was young enough to snag for herself) not to go out with Ryder, making her seem like the older version of her nurse in "A Farewell to Arms". All she has to do is pronounce "cocktail" in a unique way and profess indignance in her efforts to replace a deceased maid to steal your heart. 2000 was a banner screen year for Stritch (prior to her legendary one woman show and the TV series "30 Rock") with two other movies, and this one has her showing us the true Elaine. Had she had more footage and at least one big powerful scene, she could have been an Academy Award front runner because this is exactly the type of film they like to honor events with, especially having been passed over for deserving nominations for "Providence" and "September".

But for all of the good moments, this is a Fantasia view of the most populous city in the United States, the type of film that makes it seem like it's absolutely fabulous even though there are many elements about the city that are not explored here. Everyone seems so nice and concerned about each other, and while there are some self-centered characters, they are written with angelic layers that aren't quite realistic. The colors are all autumn related which makes you think that you are fueling a modern version of a New York set 50's movie, something like "How to Marry a Millionaire", "The Man in the Grey Flannel Suit", "Desk Set" and "The Best of Everything", or the many dozens of other Cinemascope films of that era. Anthony LaPaglia is showy as Gere's pal, and Sherry Stringfield and Mary Beth Hurt get good moments as well. Far from perfect, this is a difficult film to entirely dislike while analyzing all of the aspects, although I do see how it can make many people cringe with certain elements that I chose to overlook and forgive.

"Autumn In New York" has delectable shots of brown and golden leaves fluttering down in the winds from craggy old tree branches, covering wet sidewalks and surrounding two movie stars staring into each other's eyes. But these stars (Richard Gere and Winona Ryder) are distinctly un-New York, and the filmmakers keep everything mushy, flip and coy. Ryder looks lovely, but she giggles too much in between her incredulous comments: "REALLY?!"..."WOW!"..."AM-MAAZING!" Gere, laughing with his mouth closed, gives a bloated performance, scrunching his face while tearing up at his black, beady eyes. Anthony LaPaglia is much better in a smallish role as Gere's best friend, Elaine Strich is amusingly jaded as Ryder's disapproving grandmother (although her line about only being able to afford pistachio nuts is ludicrous when she lives in such beautiful New York digs),but this romance cops a corny plea from "Love Story", and how long ago was that? The fact that some reviewers actually fell for this is, like, AM-MAAZING! *1/2 from ****