
Jack Goes Boating
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Movies Like Jack Goes Boating
Similar in style, tone, and themes — find your next watch.

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.

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.

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.

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.

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.

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.

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.

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.

Sitting in Bars with Cake
2023★ 7.0
Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces a challenge unlike anything they've experienced before.

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.

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?

Love Don't Co$t a Thing
2003★ 7.7
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.

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.

The Incredible Jessica James
2017★ 6.1
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.

Blind
2017★ 6.1
A novelist is blinded in a car crash that killed his wife and several years later rediscovers his passion for life and writing when he embarks on an affair with the neglected wife of an indicted businessman.

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.

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.

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.

Time Is Up
2021★ 6.5
Vivien, an accomplished student with a passion for physics, and Roy, a troubled young man, are involved in an accident that forces them to reclaim their lives one minute at the time.

Friends with Kids
2012★ 6.0
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.