Best movies like How to Lose Friends & Alienate People

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20 Dates (1998)

Plot Summary:

Myles is divorced in L.A. He wants a love life and a film career. So he decides to go on 20 dates and find true love in front of a camera, making his first feature. His patient agent, Richard, finds a $60,000 investor, the shadowy Elie. Myles starts his search, sometimes telling his date she's being filmed, sometimes not. Elie wants sex and titillation, Myles wants it "real." Myles regularly talks with his old film teacher, Robert McKee, who wonders if love is possible in modern life. Half-way through the 20 dates, Myles meets Elisabeth; she's everything he desires and she likes him. Can he finish the 20 dates, satisfy Elie, and complete his film without losing Elisabeth?.

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Isn't She Great (2000)

Plot Summary:

An unsuccessful over-the-top actress becomes a successful over-the-top authoress in this biography of Jacqueline Susann, the famed writer of "The Valley Of The Dolls" and other trashy novels. Facing a failing career, Susann meets a successful promoter who becomes her husband. After several failures to place her in commercials and a TV quiz show, he hits upon the idea for her to become a writer. In the pre-60's, her books were looked upon as trash and non-printable. But then the sexual revolution hit and an audience was born for her books. The story shows the hidden behind the scenes story of Susan's life, including her autistic son and her continuing bout with cancer that she hid up to her death.

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Top Five (2014)

Plot Summary:

A comedian tries to make it as a serious actor when his reality-TV star fiancé talks him into broadcasting their wedding on her TV show.

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The Real Blonde (1997)

Plot Summary:

An aspiring actor and his girlfriend handle life's frustrations, while his friend seeks fulfillment with a blonde.

Similar in 90%

Keeping the Faith (2000)

Plot Summary:

Best friends since they were kids, Rabbi Jacob Schram and Father Brian Finn are dynamic and popular young men living and working on New York's Upper West Side. When Anna Reilly, once their childhood friend and now grown into a beautiful corporate executive, suddenly returns to the city, she reenters Jake and Brian's lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle ensues.

Similar in 75%

Broadcast News (1987)

Plot Summary:

Basket-case network news producer Jane Craig falls for new reporter Tom Grunnick, a pretty boy who represents the trend towards entertainment news she despises. Aaron Altman, a talented but plain correspondent, carries an unrequited torch for Jane. Sparks fly between the three as the network prepares for big changes, and both the news and Jane must decide between style and substance.

Similar in 79%

Not Another Happy Ending (2013)

Plot Summary:

When a struggling publisher discovers his only successful author is blocked he knows he has to unblock her or he's finished. With her newfound success, she's become too damn happy and she can't write when she's happy.The only trouble is, the worse he makes her feel, the more he realises he's in love with her.

Similar in 83%

Syrup (2013)

Plot Summary:

A slacker hatches a million-dollar idea. But, in order to see it through, he has to learn to trust his attractive corporate counterpart. Based on Max Barry's novel.

Similar in 86%

Lisa Picard Is Famous (2000)

Plot Summary:

A documentarian decides to follow the career of New York actress Lisa Picard, believing she is on the brink of fame. Instead, he bears witness to Lisa's continued, humorous, struggles as an actress, as well as the conflict that arises when Lisa's best friend Tate hits it big with an off-Broadway one-man show.

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Bridget Jones's Baby (2016)

Plot Summary:

Breaking up with Mark Darcy leaves Bridget Jones over 40 and single again. Feeling that she has everything under control, Jones decides to focus on her career as a top news producer. Suddenly, her love life comes back from the dead when she meets a dashing and handsome American named Jack. Things couldn't be better, until Bridget discovers that she is pregnant. Now, the befuddled mom-to-be must figure out if the proud papa is Mark or Jack.

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Long Shot (2019)

Plot Summary:

Fred Flarsky is a gifted and free-spirited journalist who has a knack for getting into trouble. Charlotte Field is one of the most influential women in the world -- a smart, sophisticated and accomplished politician. When Fred unexpectedly runs into Charlotte, he soon realizes that she was his former baby sitter and childhood crush. When Charlotte decides to make a run for the presidency, she impulsively hires Fred as her speechwriter -- much to the dismay of her trusted advisers.

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Life or Something Like It (2002)

Plot Summary:

A reporter Lanie Kerrigan interviews a psychic homeless man for a fluff piece about a football game's score. Instead he tells her that her life has no meaning and is going to end in just a few days, which sparks her to action, trying to change the pattern of her life.

Similar in 75%

How Do You Know (2010)

Plot Summary:

After being cut from the USA softball team and feeling a bit past her prime, Lisa finds herself evaluating her life and in the middle of a love triangle, as a corporate guy in crisis competes with her current, baseball-playing beau.

Similar in 79%

Going the Distance (2010)

Plot Summary:

Erin and Garrett are very much in love. When Erin moves to San Francisco to finish her journalism degree and Garrett stays behind in New York to work in the music industry, they gamely keep the romance alive with webcams and frequent-flyer miles. But just when it seems the lovers will soon be reunited, they each score a big break that could separate them for good.

Similar in 90%

One Fine Day (1996)

Plot Summary:

Melanie Parker, an architect and mother of Sammy, and Jack Taylor, a newspaper columnist and father of Maggie, are both divorced. They meet one morning when overwhelmed Jack is left unexpectedly with Maggie and forgets that Melanie was to take her to school. As a result, both children miss their school field trip and are stuck with the parents. The two adults project their negative stereotypes of ex-spouses on each other, but end up needing to rely on each other to watch the children as each must save his job. Humor is added by Sammy's propensity for lodging objects in his nose and Maggie's tendency to wander.

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Tootsie (1982)

Plot Summary:

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego -- Dorothy Michaels -- in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.

Similar in 88%

Bridget Jones: The Edge of Reason (2004)

Plot Summary:

Bridget Jones is becoming uncomfortable in her relationship with Mark Darcy. Apart from discovering that he's a conservative voter, she has to deal with a new boss, a strange contractor and the worst vacation of her life.

Similar in 77%

Working Girl (1988)

Plot Summary:

Witty, romantic look at life in the corporate jungle. Tess McGill is an ambitious secretary with a unique approach for climbing the ladder to success. When her classy, but villainous boss breaks a leg skiing, Tess takes over her office, her apartment and even her wardrobe. She creates a deal with a handsome investment banker that will either take her to the top, or finish her off for good.

Similar in 87%

He's Just Not That Into You (2009)

Plot Summary:

Remember that really cute guy who said he'd call – and didn't? Maybe he lost your number. Maybe he's in the hospital. Maybe he's awed by your beauty, brains or success. Or maybe... he's just not that into you.

Similar in 81%

Sex and the City (2008)

Plot Summary:

A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.

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Confessions of a Shopaholic (2009)

Plot Summary:

In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping-a little too good, perhaps. She dreams of working for her favorite fashion magazine, but can't quite get her foot in the door-until ironically, she snags a job as an advice columnist for a financial magazine published by the same company.

Similar in 85%

Adventureland (2009)

Plot Summary:

In the summer of 1987, a college graduate takes a 'nowhere' job at his local amusement park, only to find it's the perfect course to get him prepared for the real world.

Similar in 84%

The Longest Week (2014)

Plot Summary:

As he eases into adulthood at the age of forty, Conrad Valmont, the over-educated, under-employed heir to the Valmont Hotel fortune, is cut off from his allowance following his parents abrupt divorce and tossed out into the unforgiving streets of the Upper West Side. Luckily, he is taken in by his old friend Dylan, and returns the favor by immediately falling for Dylan’s girlfriend Beatrice. As Conrad attempts to woo Beatrice while keeping both their relationship and his bank balance secret, Dylan tries to set him up with Jocelyn. Ever committed to the charade that he eventually finds difficult to maintain, Conrad quickly realizes his charm can only extend so far into debt. Now deep into an extensional reflection, will it take losing everything to make Conrad realize what he can truly become?.

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Morning Glory (2010)

Plot Summary:

A young and devoted morning television producer is hired as an executive producer on a long-running morning show at a once-prominent but currently failing station in New York City. Eager to keep the show on air, she recruits a former news journalist and anchor who disapproves of co-hosting a show that does not deal with real news stories.

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Bridget Jones's Diary (2001)

Plot Summary:

A chaotic Bridget Jones meets a snobbish lawyer, and he soon enters her world of imperfections.

Similar in 87%

Love Actually (2003)

Plot Summary:

Follows seemingly unrelated people as their lives begin to intertwine while they fall in – and out – of love. Affections languish and develop as Christmas draws near.

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When Harry Met Sally... (1989)

Plot Summary:

During their travels from Chicago to New York, Harry and Sally Will debate whether or not sex ruins a perfect relationship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

Similar in 82%

Notting Hill (1999)

Plot Summary:

William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

Similar in 80%

How to Lose a Guy in 10 Days (2003)

Plot Summary:

An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.

Similar in 75%

The Devil Wears Prada (2006)

Plot Summary:

The Devil Wears Prada is about a young journalist who moves to New York to work in the fashion industry. Her boss however is extremely demanding and cruel and won’t let her succeed if she doesn’t fit into the high class elegant look of their magazine when all she really wants to be a good journalist.