Best movies like 40 is the New 20

A unique, carefully handpicked, selection of the best movies like 40 is the New 20 Starring Pat Mastroianni, Claudia Ferri, Bruce Dinsmore, Diana Lewis, and more. If you liked 40 is the New 20 then you may also like: The Velocity of Gary, Wexford Plaza, The Object of My Affection, A Date with Judy, Gone to Earth 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.

When he learns that a co-worker is friends with his old high-school girlfriend, Jennifer, stockbroker Gary helps his former flame get a job at his company in order to pursue her affections all over again. But when Jennifer rejects his advances and dates other men, Gary becomes increasingly obsessed with winning her back.

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The Velocity of Gary

When bisexual porn star Valentino meets new-in-town hustler Gary, there is an immediate attraction between the two. Valentino helps get Gary a job at a phone-sex company, and they become fast friends and lovers, but tension threatens their relationship when Gary and Valentino's friend Mary becomes involved. When Valentino finds out he is dying and Mary is going to have his child, the three must work through hard times together.

Wexford Plaza

An isolated and friendless female security guard finds a glimmer of hope when a charming bartender shows her kindness.

The Object of My Affection

A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.

A Date with Judy

Best friends Judy and Carol compete for the affection of an older man during their high school dance. As Carol tries to rekindle Judy's relationship with Carol's bumbling brother, Oogie, Judy suspects that her father is having an affair with a beautiful dance instructor. The two girls team up to expose Judy's father -- who is only taking innocent dance lessons.

Gone to Earth

Jennifer Jones plays Hazel Woods, a beautiful young English Gypsey girl who loves animals and in particular her pet fox. She is hotly desired by Jack Reddin a fox hunting squire who vies for her affection and pursues her even after her marriage to the local pastor.

Good Advice

An investment banker loses everything and must discover what's important in life.

Speed to Spare

Stunt driver Cliff Jordan takes a job with his old pal Jerry McGee, branch manager of an express trucking firm. Jerry is married to Mary, Cliff's former girl friend. Also working for Jerry is Pete Simmons, son of the owner Al Simmons, and office secretary Jane Chandler, who is Pete's sweetheart. Before long, Cliff has made enemies of Pusher Wilks, a trucker whose run he takes over, and also Pete, whose girl he is trying to take over. Pusher sabotages Cliff's rig at every opportunity causing several near-fatal accidents.

Saint Ralph

This Canadian made comedy/drama, set in Hamilton, Ontario in 1954, is a sweet and - at times - goofy story that becomes increasingly poignant as the minutes tick by. It's the fictional tale of a wayward 9th grader, Ralph (Adam Butcher), who is secretly living on his own while his widowed, hospitalized mother remains immersed in a coma. Frequently in trouble with Father Fitzpatrick (Gordon Pinsent), the principal of his all-boys, Catholic school, Ralph is considered something of a joke among peers until he decides to pull off a miracle that could save his mother, i.e., winning the Boston Marathon. Coached by a younger priest and former runner, Father Hibbert (Campbell Scott), whose cynicism has been lifted by the boy's pure hope, Ralph applies himself to his unlikely mission, fending off naysayers and getting help along a very challenging path from sundry allies and friends.

Someone Great

An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.

Stowaway

On her first night as a dockside dancer, Mary Foster loses her job when she tries to fend of the advances of first mate Groder. On the street and being pursued by a Policeman who thinks she is a prostitute, Mary seeks shelter on an old freighter. She is soon discovered by second mate Tommy and they quickly fall in love, but with first mate Groder lurking around will their lives work out in the end?

Get a Job

A recent college graduate and his friends are forced to lower life expectations when they leave school for the real world. Life after college graduation is not exactly going as planned for Will and Jillian who find themselves lost in a sea of increasingly strange jobs. But with help from their family, friends and coworkers they soon discover that the most important (and hilarious) adventures are the ones that we don't see coming.

In Your Wildest Dreams

High school senior Mark's wildest dreams come true when he makes a simulated stock purchase that accidentally turns him into a millionaire overnight. But when he discovers that the money belongs to his girlfriend's dad, who needs the funds to save his electronics company, will Mark admit to the snafu? Or will he keep the money and pursue his dreams of wealth, even if it destroys those he cares about?

Men Seeking Women

Three best friends mess up their already flagging love lives with an ill-fated bet. They each put two thousand dollars in a bank account, with the winner being the one who can not only get a girlfriend, but also live with her for three months. Nick decides to hoodwink his two friends by faking a relationship with an old girlfriend from college, while Al proceeds to embark on a series of the worst dates imaginable, and Les finds himself getting deeply involved with an alluring but mysterious woman who may or may not be married to a mobster. Hilarious antics lead to an unexpected outcome guaranteed to surprise.

Buy & Cell

Herbie Altman is framed for Stock fraud by his boss when the SEC starts investigating his company. Sent to prison, he helps a fellow inmate successfully invest his money. Soon all the inmates want his help. To manage all the money, he forms CON INC. and runs it from the prison under the noses of the warden and the guards. But when the IRS and SEC begin to investigate this successful company, it looks like he may be in trouble again

Dater's Handbook

A woman changes her personality according to a dating guide book to find a husband but realizes the man she wants is the one who loves her for who she is.

Heart of the Holidays

After her life in New York unexpectedly falls apart, powerhouse stockbroker Sam Wallace returns to her small town for the holidays and reconnects with her high school sweetheart who helps reignite her humanitarian spirit just in time to help their community on Christmas.

Walking the Dog

Kristie Simmons, an attorney, initiates a legal battle trying to get approval for a bike lane for the local residents. When Bill, a local veterinarian, informs her that a dog named Gidget needs a home, Kristie agrees. While out walking Gidget, Kristie meets Keith Amos, an attorney on assignment from Seattle, while he's walking his lovable dog, Simon. Keith is immediately smitten with Kristie, her initially pleasant reaction to him turns sour when she learns he is her opposing counsel in the bike lane case.

Married by Christmas

Due to an antiquated clause in her grandmother’s will, an ambitious young executive may lose her place at the family company unless she can get married by Christmas.

Peloton

The painful and humorous journey of a selfish athlete who is now down on his luck, unable even to keep his job as a bike messenger. He finds a way to redeem his life through the support of friends and by learning that to break from the large group of bikers, the peloton, the winning cyclist must first work with the team.

Steve Jobs: Billion Dollar Hippy

Broadly considered a brand that inspires fervour and defines cool consumerism, Apple has become one of the biggest corporations in the world, fuelled by game-changing products that tap into modern desires. Its leader, Steve Jobs, was a long-haired college dropout with infinite ambition, and an inspirational perfectionist with a bully's temper. A man of contradictions, he fused a Californian counterculture attitude and a mastery of the art of hype with explosive advances in computer technology. Insiders including Apple co-founder Steve Wozniak, the chairman who ousted Jobs from the company he founded, and Jobs' chief of software, tell extraordinary stories of the rise, fall and rise again of Apple with Steve Jobs at its helm. With Stephen Fry, world wide web inventor Sir Tim Berners-Lee and branding guru Rita Clifton, Evan Davis decodes the formula that took Apple from suburban garage to global supremacy.

The Dating List

Career driven Abby agrees to help her busy boss find the man of her dreams, but she encounters a dilemma when she starts falling for the same man her boss approves of dating.

East Bay

An odd and intense middle aged Korean American man flirts with the idea of suicide because he believes he's failed his immigrant parents. He's disturbed by his increasingly vivid hallucinations of what his life could have been. So he pursues spirituality to calm himself, and in the process encounters others who are struggling in their own ways.

The March Sisters at Christmas

To keep the family home from being sold, four very modern March sisters tackle home improvement on their own. But their romantic entanglements involving the boy next door, an old flame and a new acquaintance become a distraction.

While You Were Dating

A long-divorced couple are reunited on a blind date and agree to fix each other up with friends and colleagues. While fix-up after fix-up fails to work out for either of them, they begin to wonder if perhaps they aren't the right match for one another after all.

This Magic Moment

When Hollywood star Helena Harris (Diane Neal) films her newest movie, “This Magic Moment,” in the small town of Stone’s Throw, she strikes up an unlikely friendship with local video store owner Clark Gable (Travis Schuldt). Helena, who recently broke up with “This Magic Moment” co-star Roberto Molinez (Vincent Spano), asks her new friend Clark to pretend to be her love interest in order to make Roberto jealous. Clark agrees and in exchange, Helena helps him pursue his screenwriting career. While this agreement benefits both Clark and Helena, it also complicates the relationship between Clark and his newly single ex-girlfriend, Emily McIntyre (Alaina Huffman). As the director Doyle Duncan (Charles Shaughnessy) begins to wrap production, Clark finds himself caught between his admiration for the famous beauty and his feelings for former high school sweetheart. With whom will he find his happy ending?

Pool Boy Nightmare

The story follows Gale as she has a brief affair with pool cleaner Adam, but quickly turns down his continued advances. Insulted at being rejected, Adam starts dating Gale's high school age daughter Becca, using her as an unsuspecting pawn in a twisted game of revenge.

Deceitful Dating

John Logan, a widower and father of two daughters, is struggling to balance his job and parenting. Luckily, he has the help of Jillian, his wife’s best friend. When an attractive woman moves in across the street, John finds himself enjoying her company. Alice, the new neighbor, starts spending time at the Logan house, even helping John with the girls. This new woman in John’s life is a bit mysterious and she starts getting caught in some lies raising the suspicion of Jillian and John’s older daughter, Chelsea. When Alice’s ex-husband is found dead, everyone starts to wonder if Alice is as sweet as she seems

The Winning of Barbara Worth

While building an irrigation system for a Southwestern desert community, an engineer vies with a local cowboy for the affections of a rancher's daughter.

The Nanny Murders

A young woman reluctantly takes a job as a Nanny, for a well-known businessman. He quickly makes advances towards her, which she rejects, only for his passion to become deadly.

Tomboy

Tori, a sports agent who values winning at all costs, decides to become more feminine in order to impress her crush at work. When she finally lands the guy, she realizes she's lost not only her true self, but also the respect of those who've loved her all along.

A Girl's Best Friend

Penelope, better known as Polka-Dot, is a spunky young girl who has a knack for helping people, particularly her ailing mother. While out looking for a part-time job, Polka-Dot befriends a hard-nosed police officer and his tracking dog, Luey. When Polka-Dot's mother's condition worsens, Luey helps Polka-Dot find the strength and faith inside to help her move forward.

Advance & Retreat

Life is good for marketing professional Allison, she’s well on her way to earning a stellar promotion all while dating equally successful co-worker Bryce. Her biggest rival for the position, Vanessa, has the boss’ eye, but Allison has a plan. To win the promotion, she needs to impress her boss, Nathan, at their annual company retreat. Of course, she has a head start since she used to be a camp counselor. The only caveat, this year’s trip happens to be the site of Allison’s first heartbreak: her old camp. And who should still be working there but the handsome as ever ex-boyfriend who broke that teenage heart, Cody. But was it all a misunderstanding? Allison’s tasked with navigating not only the obstacle course but her relationships…past and present.

The Unity of All Things

The adolescent sons of an expatriated Chinese physicist visit her in the United States, while she and her colleagues pursue the development of a massive particle collider with which to understand the origin of the Universe. A queer Science Fiction, that engages the utopian impulses of the genre, not through the imagining of another world, but through the rendering of this world as Other. All subjects are treated as alien, or as radical others, who search for, or advance different ideological, psychological, or sexual ideals of belonging. Subjects oscillate between the contemplation of past societal traumas and idealizations of futurity that refuse to synthesize or resolve, but instead reveal a troubling satire of the present.

The Sweetest Heart

High school sweethearts Maddie and Nate reconnect when Nate returns to their hometown to lecture at the hospital. Still hurt from their breakup, Maddie tries to avoid him. However, they eventually form a friendship, and Nate helps her as she secures funding to expand her cupcake shop. Just as Maddie and Nate rekindle their romance, Nate learns that a career opportunity awaits him in Boston. Devastated, Maddie returns the promise ring he gave her long ago and prepares for the grand reopening of her shop. Nate soon realizes how much he left behind, and must decide if his future lies in Boston with work or in his hometown with Maddie.

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