Best movies like Jack & Jill

A unique, carefully handpicked, selection of the best movies like Jack & Jill Starring Shauna MacDonald, John Kalangis, Kathryn Zenna, Scott Gibson, and more. If you liked Jack & Jill then you may also like: Who's Been Sleeping in My Bed?, Once Around, Overnight Delivery, The Answer Man, Book of Love and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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In this lightweight Canadian romantic comedy, a couple in their thirties discovers that love in the '90s can be a messy and complicated proposition. Jack (John Kalangis, who also directs) and Jill (Shauna MacDonald) are going to get married, until Jack changes his mind and coldly announces his reluctance on a voice-mail message. The two later talk in person and decide that rather than breaking up completely, they just allow themselves to see other people. Jack and Jill find their new flings at the same bookstore. Jack takes up with Laura (Tara Johnson), a beautiful customer, while Jill becomes seriously involved with store-clerk Stephen (Scott Gibson). When Jack and Laura realize that they don't have the right chemistry for a long-term relationship, Laura decides to help him win Jill back.

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Who's Been Sleeping in My Bed?

TV star Jason Steel reluctantly becomes the sounding board for his best friends' bored wives, and must fend off their advances while managing his own fragile relationship.

Once Around

Renata Bella feels like a failure at life and career. But when Renata attends a seminar on selling real estate, she finally finds True Love. Sam Sharpe, while a top-notch, successful salesman, is much older than Renata. She is swept away by his excessively flamboyant style and irrepressible nature. The very traits she finds romantic, however, lead to repeated conflict with her family, especially her beloved father Joe, leaving Renata trapped in the middle.

Overnight Delivery

A man suspects his girlfriend of being unfaithful, so he sends her a letter, but then finds out that he was wrong. He has 24 hours to stop the package, prevent a disaster, and fall in love. The only problem is the delivery man will not stop until the package has been delivered.

The Answer Man

Twenty years ago, Arlen Faber wrote a book about spirituality that became wildly popular. These days, he's a curmudgeonly recluse who only enjoys the company of his chiropractor, Elizabeth. As Elizabeth's warmth starts to melt Arlen's cold heart, he comes to realize what love really means.

Book of Love

John Twiller takes down his high school yearbook and begins to reminiscence about that time he first moved into the neighborhood in 1956. His teenage self, Jack is obsessed with Lily one of the more popular girls around. The sole obstacle is Angelo, her bullying boyfriend. With the help of his pals Crutch, Floyd, and Spider, he makes every attempt possible to change her mind.

Come True

Looking for an escape from her recurring nightmares, 18-year-old Sarah submits to a university sleep study, but soon realizes she's become the conduit to a frightening new discovery.

Staircase

An aging gay couple owns a barber shop in the East End of London. One of them is a part-time actor about to go on trial for propositioning a police officer. The action takes place over the course of one night as they discuss their loving but often volatile past together and possible future without each other.

Seeing Other People

Ed and Alice are two months shy of getting married when she realizes that she wishes she'd had a more active love life while still single. Reluctantly, Ed agrees to have an open relationship in the months before their wedding, and initially this seems to improve their connection, particularly in the bedroom. However, as Ed and Alice get more involved in their own flings, the experiment goes awry.

Why Did I Get Married Too?

Four couples reunite for their annual vacation in order to socialize and to spend time analyzing their marriages. Their intimate week in the Bahamas is disrupted by the arrival of an ex-husband determined to win back his recently remarried wife.

A Thin Line Between Love and Hate

Nightclub manager Darnell Wright is a perpetual playboy who is almost as devoted to his job as he is to the pursuit of beautiful women. After he sets his sights on the ultra-classy Brandi Web, he launches an all-out assault to win her heart. Ultimately, charm, lust and passion prevail, but Darnell learns the hard way that when you play, you pay. Brandi is much harder to get rid of than she was to get--especially when she realizes that she has a rival vying for Darnell's affection. When he finally decides to call it quits, Brandi becomes an obsessed femme fatale stalking the new love of her life.

Take a Girl Like You

Young Jenny heads to the South of England to start a new career as a school teacher. Even before she has had a chance to settle in she meets Patrick, one of the local "lads". Within a short time she has her hands full when a number of the local boys take a liking to her. But who will be the lucky one who wins her affections?

Thieves

Martin and Sally Cramer grew up on the hardscrabble Lower East Side, where Sally still teaches; meanwhile, Martin's the head of a fancy private school. Romantic dalliances with others convince them that they're meant to be together despite their differences, a decision that's cemented, oddly enough, by an over-the-top argument that draws the police.

Big Sky River

Tara needs to go back to Parable, Montana, the place that made her the happiest, in order to move forward after a messy divorce. Her handsome neighbor presents an unexpected twist.

Company

In a series of vignettes, New York bachelor Bobby learns about the perils and pleasures of love, marriage, dating and divorce from his married friends.

Escape Clause

A man finds out that his wife has paid $10,000 to have him killed. Then both the would-be killer and the wife turn up dead ...

Anatomy of a Love Seen

A film within a film that explores love in all its painful and messy glory. Six months ago Zoe and Mal fell for each other while filming a love scene, which led to an intense, whirlwind affair, followed by a devastating breakup. Soon after their split, things get complicated when the two have to meet on set once more to re-shoot that fateful sequence.

Mistrust

Happy, beautiful and independent, Veronica enjoys being a mistress. No commitment, no strings and she never has to be vulnerable. She has carefully laid every brick in the walls of the fortress surrounding her heart. She's safe and having a great time. However, there is one person who knew her heart before those walls were erected, her best friend Brandon, who has stood by her for too many years to count. And while Veronica has tried to keep her feelings at bay, he is the one who holds the key that opens her Pandora's box of emotions.

My Girlfriend's Boyfriend

Jake can only think of one thing after being dragged to the wedding of his girlfriend's best friend. How can he get out of it? On the advice of Wes, the out-and-proud best man, he pretends to be gay and gets caught kissing Wes. Little does Jake realize he's about to get caught up in a circle of jealousy and lies. Cliff, the groom, is getting married to help solidify his hunky, soap opera star image... and to stay closeted. Yep, he s gay. And his longtime boyfriend is none other than his best man. When Cliff and Wes get pictures taken of them in a compromising position (several, in fact) it looks as though his cover might be blown. Thrown into the mix is the bride's sex crazy mother and the nosy reporter-turned-wedding photographer with a sock puppet (pop icon Deborah Gibson). What ensues is a fun, quirky and modern comedy of errors that is sure to tickle your funny bone.

Fag Hag

Fag Hag is the touching inspirational story of how two hopeless no-talent losers find each other in a cruel world, and through the strength of their deep bond are empowered to become two hopeless no-talent losers. Featuring a tour de force performance cameo by Wil Wheaton (Stand by Me, TV’s Star Trek: Next Generation) as a Christian bookstore manager, Fag Hag pays homage to John Waters while launching a bold new message to the gay community. The film is set in Hope Springs, CA where we meet Destiny Rutt (Stephanie Orff; RESPECT MY ASS), a pathological liar and last place shoe-in for the first annual Miss Hope Springs Pageant. When Destiny meets Scott Bushey – a gay drifter whose ambition is to make it big as the worlds first white HIV-positive rap star “T-Cell”, the two make fast friends and resolve “to take this town of outdated gay guys by storm!”

Love in the Villa

A young woman takes a trip to romantic Verona, Italy, after a breakup, only to find that the villa she reserved was double-booked, and she'll have to share her vacation with a cynical British man.

First Blush

Nena and Drew are a young, happy-ish married couple whose relationship is thrown off its axis when they meet Olivia. The trio's attraction to each other is undeniable, but when they become romantically involved, they struggle to navigate the complications of a polyamorous relationship. The three push each other's boundaries to the limits as they discover painful truths about who they are, what they want, and how to love in turbulent times.

Moon Dogs

Two teenage step brothers head off on a road trip across Scotland, with their relationship challenged by Caitlin, the free spirited and enigmatic girl who comes between them.

Snowballing

Bus loads of teenagers arrive to the ski resort. Each one is eager to get out on the slopes to ski and score. One problem; the owner has all the prices jacked up, secretly ripping people for the last two years he has been in charge. The police don't do anything because the Sheriff is in on the cover-up. The teens feel their only chance to even the score is at a skiing tournament where the winner is picked to in a raffle to win a bunch of prizes.

Ex-Girlfriends

Jennifer Carpenter, Kristen Connolly and Alexander Poe star in a comedy about three New Yorkers struggling to uncover the truth behind their romantic entanglements. Disheartened by his latest relationship catastrophe, Graham (Poe) attempts to rekindle the spark with his ex-girlfriend, Laura (Connolly). In the attempt to win her back Graham discovers he has a unique problem: Laura and another one his ex-girlfriends (Carpenter) are dating the same guy.

Single In South Beach

Amy, an attractive woman, confuses love with money and becomes a victim of the materialistic lifestyle of South Beach. Her relationship with Nick, a down-to-earth, young architect is great, but Amy has dreams that he can't fulfill and afford. In her search for glamour and a dancing career, Amy meets Sam, an older, married man. Even though Sam provides her with the luxurious lifestyle, she begins to feel a void for love and attention. Unwilling to let go of Sam's financial support, Amy becomes involved in another relationship with Robert, who grows suspicious. Amy soon discovers that life in South Beach, not everything is as good as it looks.

Should've Put a Ring On It

Robin Givens, Miguel Nunez, and Bobby Valentino star in this faith-based romantic drama about Thea Johnson, terribly desperate to be married to her longtime boyfriend Jamar. When he takes too long to propose, she decides to propose to him instead. Thea creates an elaborate proposal, but is thwarted by his reluctance. An obsessed ex-boyfriend, married & single friends, and Thea s father & pastor all take part in the tug of war for her heart.

Heaven Sent

As Christmas approaches, the end is near for Billy and Marie's marriage until an eight-year-old runaway angel from heaven takes it upon herself to rekindle the love they once shared.

From Zero to I Love You

Darryl Stephens plays Pete Logsdon-just a guy in Philadelphia who happens to have a history of getting involved with married men. His father, played by veteran Richard Lawson and his soon-to-be step mom, Leslie Zemeckis, are on him to find someone who's actually available and to settle down. Instead, he finds a man named Jack who is fifteen years into a perfect marriage with two beautiful children and an enviable wife.

Cor, Blimey!

Dramatisation of the love affair between Sidney James and Barbara Windsor, played out against the backdrop of the 'Carry On' films during the 1960s and 1970s.

Tru Love

TRU, 37, is a serial bed-hopping lesbian who cannot commit to a relationship or a job for long...that is, until she meets ALICE, 60, a beautiful widow, who has come to town at the last minute to visit her daughter, SUZANNE, 35, a too-busy corporate lawyer and Tru's friend. Alice and Tru begin to forge an unlikely friendship...and more. Suzanne, who has a deeply conflicted relationship with her mother and a complicated past with Tru, becomes increasingly alarmed at the growing bond between Tru and her mother. Tensions escalate after Suzanne witnesses an intimate moment between them. She tries to sabotage the budding romance, but it backfires, as Tru Love is hard to contain.

Best Friend from Heaven

When a tragic accident takes the life of her dog, Tara is forced to cancel her wedding. With a little help from above, their small town rallies together to make sure these two are able to have the wedding of their dreams.

Lead with Your Heart

Ben and Maura have been married for years, and they are in a rut…so much of a rut that they are contemplating if it would be better to live separate lives. That’s when their two teenage children step in and scheme to try to get them back together and make them realize how much they still need each other.

Love, Take Two

Lily produces a wedding reality show, but her success driven world is flipped when her ex, Scott, is cast as groom-to-be. Lily must revisit her past if she's to find her own happily ever after.

Love and Magnets

Back in Montréal after spending five years in Guatemala, Julie moves in with her elder sister, Jeanne, a chronic liar and woman of rather loose sexual morals... Disillusioned with love, Jeanne is nevertheless engaged to Noël. However, Jeanne and Noël lead separate lives, and only communicate by leaving each other messages on the fridge.Everything suddenly becomes very complicated. Jeanne compels Julie to take up with Noël so she can have a fling with a passionate musician. Noël, meanwhile, sets Julie up with Michel -- without Jeanne's knowledge. Julie mixes things up even further. Egged on by her friend Marie-Ève, she alters the contents of the messages on the fridge in an attempt to breathe new life into Jeanne and Noël's relationship. Along the way, she also begins to fall for the seductive Michel. The tables are turned on everyone... In the game of love and truth, illusion leads to betrayal, but love conquers all.

Which Brings Me to You

Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.

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