Autumn in New York (2000)

Name: Autumn in New York
Released: 2000

Will Keane, a Manhattan restaurateur, is content with his playboy lifestyle until he meets Charlotte Fielding, a free-spirited young woman. Together the pair pursue a passionate affair that forces them both to reevaluate what they want out of life, even as fate threatens to steal away their future.

Genres: Drama, Romance

What to watch after Autumn in New York

Nights in Rodanthe (2008) — Same feel: emotional, sad
Intersection (1994)
Mr. Deeds (2002) — Same subject: love
September (1987) — Same feel: emotional, sad
How to Make an American Quilt (1995)
Final Analysis (1992) — Richard Gere appears in both