Best movies like Gray Matters

A romantic comedy about a brother, a sister and the girl of their dreams.

A unique, carefully handpicked, selection of the best movies like Gray Matters Starring Heather Graham, Bridget Moynahan, Tom Cavanagh, Alan Cumming, and more. If you liked Gray Matters then you may also like: Nina's Heavenly Delights, Relax... It's Just Sex, Jenny's Wedding, Kiss the Bride, All Over Me 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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Sam and Gray are such a well-matched pair that it is difficult to believe they are brother and sister rather than husband and wife. They both share a love of 1940s movies and dancing, and when they meet Charlie, they have something else in common: They both fall in love with her. Sam must deal with unexpected feelings of jealousy, while Gray struggles to come to terms with her sexual orientation.

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Nina's Heavenly Delights

A feisty young woman returns to Glasgow to run her deceased father's curry house.

Relax... It's Just Sex

A tight-knit group of thirty-somethings -- gay, lesbian and straight -- struggle to live, love and stay friends in modern-day Los Angeles as circumstances conspire to tear them apart.

Jenny's Wedding

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

Kiss the Bride

In high school, Matt and Ryan were best friends. More than friends, actually. But in the ensuing ten years, they've lost contact. So when Matt receives an invitation to Ryan's wedding he's surprised - especially that Ryan is marrying a woman!

All Over Me

Claude and Ellen are best friends who live in a not-so-nice area of New York. They're involved in the subculture of 90s youth, complete with drugs, live music, and homophobia. All is changed one night when a violent and meaningless death rocks their lives.

Am I Ok?

Lucy and Jane have been best friends for most of their lives and think they know everything there is to know about each other. But when Jane announces she's moving to London, Lucy reveals a long-held secret. As Jane tries to help Lucy, their friendship is thrown into chaos.

Better Than Chocolate

Not long after moving into her own place, Maggie finds herself with two unsolicited roommates: her recently divorced mother, Lila, and her young brother. The timing is especially bad, considering Maggie has fallen hard for an attractive woman, Kim, only hours before they move in. What could be a nonissue becomes increasingly complicated -- since Maggie's family is unaware of her sexual orientation, and Maggie is not open to sharing that information.

Boyfriends

Paul, Matt, and Will (in their 30s) have been friends for years. They converge at the seaside for the weekend, each with a boyfriend in tow. Paul is with Ben, his companion of five years: their relationship is on the rocks after months of Paul's moodiness since his brother Mark died. Matt brings Owen, whom he's dated for three months and wants to live with; to everyone else, they seem singularly.

The Cabin Movie

Three couples travel to a secluded cabin in an attempt to revitalize their lives through bizarre games of sexual dysfunction....and all heck breaks loose!

Cake

A travel writer improves her love life when she becomes an editor for her father's wedding magazine.

An Unexpected Love

An unhappily married housewife and mother of two children seperates from her husband and gets a new job where she developes a mutual attraction to her female boss.

Elena Undone

The wife of a pastor who preaches against homosexuality embarks on an affair with a female writer.

The Incredibly True Adventure of Two Girls in Love

An adventurous love story between two young women of different social and economic backgrounds who find themselves going through all the typical struggles of a new romance.

Imagine Me & You

During her wedding ceremony, Rachel notices Luce in the audience and feels instantly drawn to her. The two women become close friends, and when Rachel learns that Luce is a lesbian, she realizes that despite her happy marriage to Heck, she is falling for Luce. As she questions her sexual orientation, Rachel must decide between her stable relationship with Heck and her exhilarating new romance with Luce.

5.9 / 10 1997 Romance Comedy
suggested by: user800o0xvw5hc

It's in the Water

When hordes of gays and lesbians come out "of the closet" in the fictional town of Azalea Springs, Texas, intolerant residents go into a panic about the water supply.

Parting Glances

Michael and Robert, two gay men living in Brooklyn, spend their last day together before Robert leaves for Africa on work assignment. Michael still has feelings for his friend Nick, who has AIDS.

The World Unseen

A drama centered on two women who engage in a dangerous relationship during South Africa's apartheid era.

The Sex Monster

A neurotic L.A. building contractor (Mike Binder in his best Woody Allen imitation) pushes his wife (Mariel Hemingway) into entering into a three way sexual relationship. Unfortunately for him, his wife gets more out of it than he does and becomes a tigress seducing every female she meets including the contractor's secretary.

Sleep with Me

Six different writers wrote a scene each of this romantic comedy featuring the marriage and turbulent relationship of Joseph and Sarah, with Joseph's best friend Frank trying hard to cope with letting the love of his life marry his best friend.

City of Trees

A 20-something woman goes back to her hometown for the holidays for the first time in several years and is not only met with people from her past, but she's forced to deal with unresolved feelings too.

Desert Hearts

The story of straight-edge literature professor Vivian who travels to Reno to get away from a relationship breakup when she falls in love with an attractive and unconventional girl named Cay.

The Misadventures of Margaret

A timid, insecure popular author with an overly-attentive professor husband decide to write an erotic novel. With encouragement from her sister and a bi-sexual friend, she goes to France with the intent of doing research at an inn where a diary she had been using documented erotic encounters. Instead she finds the inn is now a cloister for singing nuns. However, a young, divorced sound engineer is also there taping the nuns. While attracted, she mostly succumbs only to new fantasies until he follows her home to New York.

I Can't Think Straight

Tala, a London-based Palestinian, is preparing for her elaborate Middle Eastern wedding when she meets Leyla, a young British Indian woman who is dating her best friend. Spirited Christian Tala and shy Muslim Leyla could not be more different from each other, but the attraction is immediate and goes deeper than friendship. But Tala is not ready to accept the implications of the choice her heart has made for her and escapes back to Jordan, while Leyla tries to move on with her new-found life, to the shock of her tradition-loving parents. As Tala's wedding day approaches, simmering tensions come to boiling point and the pressure mounts for Tala to be true to herself.

Broadway Damage

A quirky, romantic comedy about the complexity and frustration of finding a true love in the gay community. Marc is a struggling actor who finds an apartment in NYC by searching the obituaries. He lives with his out-of-work, eccentric fag-hag Cynthia. His best friend, Robert, is secretly in love with Marc, while Marc falls head over heels for flighty studio musician David. Things heat up as Marc's desire for David keeps him waiting by the phone, while Cynthia gets financially cut off from her rich parents and Robert struggles to express his feelings for Marc.

Drool

An abused wife's plan to escape her husband goes awry when she accidentally kills him, causing her to split on a cross-country drive with her best friend and his corpse in tow.

The Truth About Jane

Jane, a high school teenager, tries to deal with the discovery that she is a lesbian after developing an intense friendship with another girl who makes her discover her true sexuality, which is only the start of Jane's troubles when Jane's unaccepting mother, Janice, struggles with her surprising revelation of brought forth by her only daughter.

Losing Chase

An intimate and turbulent relationship develops between Chase, a woman recovering from a nervous breakdown and Elizabeth, the caretaker employed to look after her.

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.

The Guest House

Before leaving for college, a recently dumped goth girl's life changes forever when she falls in love with a smart and professional college grad who is staying in the family's guest house.

Raven's Touch

Blaming herself for a tragic accident, Raven Michaels secludes herself at a remote family cabin. She wanders the woods on the verge of a breakdown, seeking peace in isolation. In a last ditch attempt to save her family, Kate Royce takes her two teenagers camping far from the distractions of technology and young romance. When Raven and Kate's worlds collide they offer each other unexpected opportunities for intimacy and healing.

Ambrosia

Ambrosia is the story of an Iranian-Canadian couple, Ali and Leila, who dream of an exciting future in Vancouver: Ali owns a pizza shop and thinks of expanding and Leila is an up-and-coming clothing designer. However, their situations change dramatically when Ali's shop is affected by bad economy and Leila is hired to work at a fashion design firm.

Go Fish

Max is a trendy, pretty, young lesbian, who is having trouble finding love. A friend sets her up with Ely, whom Max likes, but Ely is frumpy, homely, and older. Nor do they have much in common. Can Max learn to look past the packaging?

Claire of the Moon

Claire of the Moon is set in the 1990s in the Pacific Northwest. Claire Jabrowski, a famous heterosexual author, decides to attend a retreat for all-female writers. Claire's rommate at the retreat is Dr. Noel Benedict, author of a book called The Naked Truth. The movie culminates in a sexual encounter between the two authors.

My Little Friend

Two friends reunite in after ten years and one has a secret waiting to come out.

A Four Letter Word

Six people in New York are adrift. Zeke and Luke work in a sex shop: Zeke takes gay liberation seriously, Luke likes to sparkle and takes nothing seriously. He's offended when Stephen calls him a gay cliché, then, surprisingly, they find each other attractive and interesting. Stephen, it turns out, has a great apartment, trust fund, and artwork he's painted on his walls. Meanwhile, Peter, a neat-freak, and Derek, nice to everyone, move in together. Peter's compulsiveness threatens the relationship. Last, newly-engaged Marilyn, a recovering alcoholic stuck at step 2, can't stop obsessing about wedding details. Can these folks sort out civilization and its discontents?

Bloomington

A former child actress attends college in search of independence and ends up becoming romantically involved with a female professor. Their relationship thrives until an opportunity to return to acting forces her to make life-altering decisions.

Maggie and Annie

Annie has it all in life. A wonderful husband and a darling little girl. All is going well until she goes to a softball practice and meets Maggie. Maggie -- cute, athletic, and openly gay -- touches feeling deep down inside Annie that she has no idea existed. Maggie also is attracted to Annie but vows to her friends that she will not make a move on her because of her wonderful family. As the friendship gets closer and as they struggle to stay apart, all hell breaks loose. A night of dancing and drinking puts Annie in the arms of Maggie. The love affair begins and reaches a point where there may be no way back.

The Four-Faced Liar

A story of love and lies for four twenty-somethings looking to find themselves in New York City. A pair of best friends and a seemingly perfect couple meet at a local Irish pub tucked in the winding streets of the West Village. Through their chance meeting, the four bond and over time all of their relationships with one another morph into love, betrayal and heartbreak for all.

Love on the Side

Small town waitress Eve Stuckley is stuck. She has spent years pining for testosterone saturate local hunk Jeff Sweeney and yearns to escape from the Hog-Chow Diner she runs. Just when Eve finally decides to pursue her man, drop dead gorgeous Linda Avery blows into town on the hottest day of the year. The heat wave is nothing in comparison with the heat that's on as Jeff and Eve's dimwitted brother Chuck decide to face off for Linda's affections. It's a priceless contest: Linda wants Eve. Eve's confidante Alma Kerns is a sex expert trained by mortician beau Red Bishop. She encourages Eve to use Linda's interest in her to win Jeff's affection but the situation becomes even more complicated when Linda advises Jeff she prefers Eve. Now determined to "save" Eve, the narcissistically injured Jeff elicits Chuck's aid but Chuck, thinking it's part of the game, refuses to believe him. Ultimately, Jeff and Linda square off over Eve's future...

April's Shower

April's Shower begins with a group of people gathered for a wedding shower for April. At first, it seems to be a normal gathering for such an occasion but, as time goes on, secrets and stories begin to be revealed. Alex is a chef and a maid of honor at April's wedding. She ultimately reveals her true feelings which ends up taking an effect on everybody at the shower.

Puccini for Beginners

When her inability to commit leads to a breakup with her girlfriend, opera-loving writer Allegra winds up in the bed of amiable professor Philip. He is so smitten with Allegra that he dumps his lover, Grace, and convinces Allegra to continue their affair. When Allegra meets Grace, sparks fly, and she begins a parallel romance, unaware that her new lover is the woman Philip left to be with her.

5.1 / 10 2015 Drama
suggested by: MysticMallard

That's Not Us

Three twenty-something couples, one gay, one lesbian, and one straight, travel to a beach house to enjoy the last days of summer, but what should be a fun and carefree weekend becomes an exploration of what it takes to sustain a healthy relationship.

Fish Without a Bicycle

Julianna is a struggling actress in a dead end relationship with Danny, a fireman who no longer lights her fire. When she decides to leave him and go "find herself" she ends up falling in love with an egotistical director, Michael, who can barely fit her in between Pilates classes.

I Hate New Year's

Rising music star Layne heads home to Nashville for New Year's Eve to break her writer's block, but sometimes you find inspiration - and love - where you least expect it.

Love or Whatever

Corey had it all - a successful career, bags of charm and, most of all, a bright future with his boyfriend. But, when his other half commits the ultimate betrayal and dumps him for a woman, he embarks upon a wild journey of self-discovery. Soon, he meets a potentially perfect new guy but first he needs to make some life-changing choices.

Jamie and Jessie Are Not Together

Jamie is moving in two weeks from Chicago to New York hoping to become a Broadway actress. Her best friend Jessica is bummed because she's not-so-secretly in love with Jamie. As moving day gets closer, Jessica tries to make Jamie jealous by dating other girls. But Jessica's plan backfires, in a way she could never imagine. Set in working class Chicago and infused with musical dance numbers, "Jamie and Jessie are Not Together" is a love letter to those gray areas of love and lust and to the young romances we will never forget.

Keep the Lights On

Documentary filmmaker Erik and closeted lawyer Paul meet through a casual encounter, but they find a deeper connection and become a couple. Individually and together, they are risk takers — compulsive, and fueled by drugs and sex. In an almost decade-long relationship defined by highs, lows, and dysfunctional patterns, Erik struggles to negotiate his own boundaries and dignity and to be true to himself.

Heartland

A young Oklahoma artist, struggling with a recent death, finds escape in a reckless affair with her brother's girlfriend.

The Dark Side of Tomorrow

While their husbands are away on work trips, two bored housewives get together to commiserate. One thing leads to another, and they wind up in bed. For one of the women the incident was just a pleasant diversion, but for the other it's turned into a fixation, and when she sees her "lover" going after one of the male neighborhood hunks, things take a turn for the worse.

Out of Season

Hip lesbian Micki Silva leaves her fast-paced urban lifestyle for Cape May, New Jersey, to help her ailing uncle Charlie. At the local diner, run by Shelley, Micki meets Charlie's friend Roberta. Roberta likes her house, working at the diner, and numerous aspects of the small-town way of life that bore Micki, but opposites attract. Drawn together by the dying Charlie, the two women develop a complex relationship.

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