
Catch and Release(2006)
For a grieving fiancée, learning to love again requires the help of her late love's three best friends.


“In a city of 8 million people, what are the odds the perfect two will meet?”
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

Edward Burns
Tommy

Heather Graham
Annie

Rosario Dawson
Maria

Dennis Farina
Carpo

Brittany Murphy
Ashley

David Krumholtz
Ben

Stanley Tucci
Griffin

Callie Thorne
Sue

Aida Turturro
Shari

Kathleen Doyle
Katy
Sidewalks of New York is a comedy, drama, romance film released in 2001. Directed by Edward Burns, it stars Edward Burns, Heather Graham, Rosario Dawson. The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
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We found 15 movies similar to Sidewalks of New York
If you enjoyed Sidewalks of New York, you'll love these handpicked recommendations. Each title below shares similar themes, tone, and storytelling style. Our algorithm analyzes genres, keywords, director filmography, and cast connections to find the closest matches. Whether you're looking for the same emotional depth, narrative structure, or visual style, these picks are curated to deliver the best viewing experience for fans of Sidewalks of New York.

For a grieving fiancée, learning to love again requires the help of her late love's three best friends.

A thief on the run convinces a single father that he is his long-lost son. Complications ensue when he falls in love with his newfound "sister".

When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quirkiest citizens scramble for a seat on his couch. As he lightens hearts darkened by old secrets no one realizes he's hiding a whopper of his own, or that he's fallen head over heels for one of his patients!

Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.

Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children, while she's in her thirties, alone with job she's outgrown and a mother who constantly reminds her of it all. Not to mention her best friend Audrey's "perfect marriage". But after a series of disastrous dates, Nora unexpectedly meets Julien, a quirky Frenchman who opens her eyes to a lot more than love.

Professor Lawrence Wetherhold might be imperiously brilliant, monumentally self-possessed and an intellectual giant -- but when it comes to solving the conundrums of love and family, he's as downright flummoxed as the next guy.

The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.

Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.

A car magnate watches his personal and professional life hit the skids because of his business and romantic indiscretions.

With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.

Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.

A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.