Sidewalks of New York
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.
Movies Like Sidewalks of New York
Similar in style, tone, and themes — find your next watch.
Young People Fucking
2007★ 5.8
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?
The Giant Mechanical Man
2012★ 6.5
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.
Mumford
1999★ 6.5
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!
Numb
2007★ 5.9
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.
Cyrus
2010★ 5.9
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.
He Said, She Said
1991★ 5.9
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.
The Best You Can
2025★ 7.0
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Cosi
1996★ 6.2
Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.
Breaking & Exiting
2018★ 6.0
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self discovery and love.
XX/XY
2002★ 5.9
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
Strictly Sexual
2008★ 6.1
Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.
Jack Goes Boating
2010★ 6.0
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Delirious
2007★ 6.4
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.
The Good House
2021★ 6.2
When wry New England realtor Hildy Good rekindles a romance with her old high-school flame, Frank Getchell, it ignites long-buried emotions and family secrets that propel Hildy toward a reckoning with the one person she's been avoiding for decades: herself. Based on the best-selling novel by Ann Leary.
How to Please a Woman
2022★ 6.2
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
Night Owls
2015★ 6.2
After workaholic Kevin has a drunken one night stand with the beautiful train-wreck Madeline, he's horrified to discover that she's actually his boss' jilted ex-mistress. When she takes a bottle of sleeping pills, Kevin is forced to keep her awake... and over the course of the night the two begin to fall for each other.
Cherry
2010★ 6.2
Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.
Extracurricular Activities
2019★ 6.1
The outrageous life of Reagan Collins, a model high school student with a "killer" after-school job that involves arranging “accidents” for his classmates' parents. When seasoned police detective Cliff Dawkins starts putting the pieces together, it's a battle of wits to see if Reagan can keep business booming.
Enemies, a Love Story
1989★ 6.2
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Love & Sex
2000★ 6.1
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.