Best movies like Love on the Side

A small-town waitress vies with a sassy city slicker for the attention of the town's most eligible bachelor.

A unique, carefully handpicked, selection of the best movies like Love on the Side Starring Marla Sokoloff, Jennifer Tilly, Monika Schnarre, Dave Thomas, and more. If you liked Love on the Side then you may also like: What Love Is, Nina's Heavenly Delights, On_Line, On the Line, Replay 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.

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...

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What Love Is

It's Valentine's Day and Tom has big plans. He's about to get engaged and has a surprise party planned to share the good news with friends. But things take a turn for the worse. Tom returns home only to discover his girlfriend has packed up and left him. Now, instead of a surprise party, the surprise is on Tom. Fortunately, his friends are there to help him make sense of it all.

On_Line

John, a computer whiz on the rebound from a disastrous break-up, starts an adult Internet site with his roommate, Moe. They are soon caught up in the erotic nature of the chat sessions they host, changing both their lives.

On the Line

A young man (Bass) is smitten with a girl (Emmanuelle Chriqui) he meets on a subway train and spends the rest of the movie trying to reunite with her. The man's best friend (Fatone) helps him in his quest by wallpapering Chicago with posters and signs that soon become the talk of the town.

Replay

Nathalie and Louise are friends from childhood. While studying drama at University Louise becomes hopelessly obsessed with her friend. Jealous of the male friends she has she breaks up the friendship, followed by a suicide attempt. Later, Louise marries, but finds time to see the, by now quite accomplished actress, Nathalie. They fight through the years, La Repetition following them as their friendship comes together and breaks up frequently, while never actually reaching anything that can be called a climax.

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.

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.

Cake

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

Chance

'Chance' is a black comedy about how hard it is to find "the one". Mostly told from the point-of-view of a young, sexually aggressive woman, named Chance, whom according to her: "we're all out there looking for true love", which turns out to be a very elusive thing indeed, and Chance is no exception. She's desperately on the prowl for a man, but since she's more mouse than cat, she gets herself into scrape after scrape in her screwball pursuit of love. Surrounded by a bevy of adoring but completely wrong-for-her men (and one dead girl from Manchester, England), Chance has to pick her way through her messy life in order to figure out which guy is "it".

The Love Letter

A romantic comedy about a mysterious love letter that turns a sleepy New England town upside down.

Get Real

Steven spends his school days longing for all-star athlete John. But John has a gorgeous girlfriend, and Steven is still in the closet about being gay. The only one who knows the teenager's secret is his friend Linda. After a curious run-in with John in a public restroom, Steven starts to wonder if the jock is straight after all. When they start a romance, it threatens to expose the truth about both of them.

Girl Play

Two real-life lesbian actresses meet by chance when they are cast as lovers in a local stage play, and end up actually falling in love. Robin, who is married to her girlfriend for half a dozen years, and Lacie, someone who never had a lasting relationship, are both cast to play lesbian lovers in a Los Angeles stage play. Innocently, the stage director, Gabriel runs the actresses through a series of rehearsals designed to "bring out the intimacy" in each performer. Soon the two women find themselves increasingly and undeniably attracted to each other and overcome with desire. They must ask themselves whether this relationship is manufactured, created for the sake of the "girl play", or is true love.

Elena Undone

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

Gray Matters

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.

Circumstance

A wealthy Iranian family struggles to contain a teenager's growing sexual rebellion and her brother's newfound conservatism.

I Hate Valentine's Day

A love story set in Manhattan, where a florist who abides by a strict five-date-limit with any man finds herself wanting more with the new restaurateur in town.

I've Heard the Mermaids Singing

Awkward, shy and delightfully funny, Polly Vandersma is an "organizationally impaired" temporary assistant who finally gets her first permanent job at the age of 31. While she works for the curator of an art gallery, Polly narrates her own story, sharing the comical and bittersweet pretensions of the art world. At the same time, she reveals a special part of her own private world, taking the viewer to enchanted places in this quiet assault on the notion of authority everywhere.

5.9 / 10 1997 Romance Comedy
suggested by: user728b0u7oiam

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.

Saving Face

A Chinese-American lesbian and her traditionalist mother are reluctant to go public with secret loves that clash against cultural expectations.

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.

Splendor

Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

Threesome

At a sizable public college, high-minded student Eddy is forced to room with the slovenly Stuart, but the pair strike up a surprising friendship. When attractive co-ed Alex is assigned to live with the two male students because of her gender-neutral name, a roundabout love triangle ensues. Eddy secretly yearns for Stuart, who wants Alex, but she prefers Eddy. The complex situation leads to sexual experimentation and strained relationships.

Tick Tock Lullaby

A wry interweave film about baby making and how as time marches on the decision gets more intense and less romantic.

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.

Tru Loved

Recently relocated from San Francisco to conservative suburbia by her lesbian mothers, Tru struggles like all teens to fit in and find love, but her quest is complicated by sexual politics, closed minds, and closeted friends as she seeks to establish her school's first Gay-Straight Alliance.

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.

The Perfect Family

Kathleen Turner stars as suburban mother and devout Catholic Eileen Cleary, who has always kept up appearances. When she runs for the Catholic Woman of the Year title at her local parish, her final test is introducing her family to the board for the seal of approval. Now she must finally face the nonconformist family she has been glossing over for years...

Funny Story

Aging TV star Walter Campbell's attempts to break up with younger girlfriend Lucy are thwarted by the announcement of her pregnancy. Looking for space, Walter resolves to visit his estranged daughter Nic, currently residing in Big Sur, resentful of her father's neglectful parenting and womanizing ways. He agrees to give a lift to Nic's friend Kim, who having recently attended the funeral of her estranged mother, is dealing with her own emotional baggage. Upon arriving in Big Sur, Walter discovers that Nic is living on a lesbian commune, and is in fact due to get married. Nic is appreciative of Walter's acceptance of her sexuality, which sees the pair's relationship begin to repair, but this newly formed bond is at risk of being destroyed once and for all.

Long-Term Relationship

Tired of the unsatisfying singles scene, Glenn answers a personal ad and meets Adam, a handsome Southern man seeking a long-term relationship. The two hit it off immediately, but their initial attraction is soon put to the test. Glenn's gay friends say he'd be happier playing the field again, but his straight pals encourage him to work at the budding relationship.

Late Bloomers

High School basketball coach, Dinah Groshardt, falls for the school secretary, Carly Lumpkin, and upsets the entire school in the process.

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.

Amy's Orgasm

Amy is a single 29 year old Jewish woman. She wrote a successful self-help book about how women can't truly be in love and experience "mental orgasm." Her parents and acquaintances always try to give her advice. Eventually, she breaks her celibacy and starts dating a radio shock jock, who is known for hitting on his bimbo guests. Of all men, will she find in him the true love she never believed in

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.

Hairshirt

A self-obsessed man runs through one woman after another in this screwball comedy. One of his rejected former lovers decides to take it upon herself to see to it that he never develops another relationship.

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?

6.4 / 10 2000 Comedy Romance
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In the Weeds

It's Martha's first night as a waitress in an upscale New York restaurant. Veteran Chloe shows her the ropes and introduces her to the lives of the restaurant staff. Adam, a hopeful playwright, suffers for his art while dealing with a very indecisive (ex-?)girlfriend. Marlon is a cocky young actor, certain that his big break is just around the corner. When the restaurant's obnoxious owner, Simon, brings a special client in for dinner, pressures mount until an explosion seems inevitable.

The Baby Formula

Two adventurous women in love are desperate to have their own biological child. They take a chance on an experimental scientific process and make sperm from their own stem cells. Pregnant with humor and unexpected twists, their journey ultimately confirms that all life is a gift and all families are crazy.

Butch Camp

A mild-mannered gay man, tired of being pushed around by straights, enrolls in "Butch Camp," a program designed to turn wimpy gay men into assertive, confident gay men.

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.

4.9 / 10 2003 Comedy Romance
suggested by: user208pee78u0n

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.

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.

200 American

Conrad is a gay man living in NYC. He's also CEO of an ad agency and by nature a control freak. Although Conrad is still in love with Martin (his ex), he hires a young Aussie hustler named Tyler, first for a night and then to work for his company. Things get increasingly complicated as Conrad tries to rekindle things with Martin. Meanwhile Tyler (who's daytime name is Ian) falls for Michael his new supervisor

Finding Me

Faybien Allan has it all going on; he's young, stylish, and knows the importance of being seen with hip friends at NYC's trendiest spots. But beneath the sparkle of his nightlife and his stunning good-looks, is a man buckling under his father's homophobia. Filled with self-loathing and desperate for direction, he meanders through life until meeting Lonnie, a confident activist with a flirtatious smile. However, despite their obvious chemistry and fireworks in bed, Faybien's insecurities have him looking for the door. Can a budding romance and a few good friends keep him from making the biggest mistake of his life?

Stud Life

Stud lesbian JJ works with her gay best friend Seb as wedding photographers. When JJ falls in love with a beautiful diva, JJ and Seb's friendship is tested, and she’s forced to chose between her hot new lover and her best friend.

Hard Pill

A despondent gay man throws his life and relationships into turmoil when he volunteers for a controversial pharmaceutical study for a drug designed to make gay men straight.

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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