Best movies like My Dear Secretary

He chased her . . . 'til she caught him!

A unique, carefully handpicked, selection of the best movies like My Dear Secretary Starring Laraine Day, Kirk Douglas, Keenan Wynn, Helen Walker, and more. If you liked My Dear Secretary then you may also like: The Wedding Night, Woman of the Year, Our Blushing Brides, The Owl and the Pussycat, Rich and Famous 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.

A budding young writer thinks it's her lucky day when she is chosen to be the new secretary for Owen Waterbury, famous novelist. She is soon disppointed, however, when he turns out to be an erratic, immature playboy. Opposites attract, of course, but not without sub-plots that touch on competitiveness within marriage and responsibility.

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The Wedding Night

While working on a novel in his country home in Connecticut, married writer Tony Barrett (Cooper) becomes attracted to Manya (Sten), the daughter of a neighboring farmer. Manya is unhappily engaged to Frederik (Bellamy). Due to a snowstorm, Tony and Manya are trapped together in his house overnight. The next day, Manya's father insists her wedding to Frederik take place in spite of Manya's misgivings. Drunkenness and jealousy result in tragedy at the wedding reception that night.

Woman of the Year

Rival reporters Sam and Tess fall in love and get married, only to find their relationship strained when Sam comes to resent Tess' hectic lifestyle.

Our Blushing Brides

Three department store girls--Connie, Franky, and Gerry--share an apartment on West 91st Street in New York City. Each earns little more than 20 dollars per week. Gerry is the sensible one, but the others throw themselves at amoral rich men in an attempt to hook one and better themselves. They end up being hurt and disappointed despite Gerry's attempts to warn them.

The Owl and the Pussycat

Meek, owlish Felix and strident, catty Doris live in the same apartment building. His incessant typing bothers her; her gentlemen callers bother him. Felix informs the landlord of her activities, so Doris moves in on Felix. When they both get thrown out, they move in with Barney... until they drive him out! That's when Felix and Doris finally decide to put theory into practice. But do opposites attract?

Rich and Famous

Two literary women compete for 20 years: one writes for the critics; the other one, to get rich.

Alex & Emma

Writer Alex Sheldon must finish his novel within a month. If he doesn't, he won't get paid. And, if that happens, angry Mafia types to whom he owes money will come looking for him. In order to expedite things, Alex hires typist Emma Dinsmore and begins dictating his novel. The book is about a doomed love affair between a character similar to Alex and a character named Polina Delacroix. But, as Alex falls for Emma, his work takes a different turn.

Angel Face

An ambulance driver gets involved with a rich girl that might have a darker side.

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.

Thanks for the Memory

Steve Merrick is an out of work writer who stays home and plays house husband while his wife goes to work for her former fiancé and Merrick's publisher who is still carrying a torch for her.

The Shopworn Angel

During WWI Bill Pettigrew, a naive young Texan soldier is sent to New York for basic training. He meets worldly wise actress Daisy Heath when her car nearly runs him over.

A Fine Madness

A womanizing poet falls into the hands of a psychiatrist with a straying wife.

Funny Farm

Sportswriter Andy Farmer moves with his schoolteacher wife Elizabeth to the country in order to write a novel in relative seclusion. Of course, seclusion is the last thing the Farmers find in the small, eccentric town, where disaster awaits them at every turn.

Grand Slam

A Russian waiter in New York City becomes a national celebrity after he develops a "system" for winning at contract bridge.

Hands Across the Table

A manicurist and an engaged loafer, both planning to marry money, meet and fall in love.

Mother

A neurotic, twice-divorced sci-fi writer moves back in with his mother to solve his personal problems.

You Hurt My Feelings

A novelist's longstanding marriage is suddenly upended when she overhears her husband giving his honest reaction to her latest book.

Purple Violets

Patti Petalson is a promising writer, but her marriage and conventional job keep her from her dream. She longs to return to her writing, especially after running into her first love Brian Callahan, a successful crime novelist. Kate is Patti's best friend since college; she's a tough-talking schoolteacher who plays therapist to all Patti's problems, while she's got a few of her own.

Christmas Ever After

Popular romance novelist Izzi Simmons spends every Christmas at her favorite snowy bed & breakfast, but this year, she's faced with an impending deadline and a severe case of writer's block. Luckily, inspiration strikes in the unlikely form of the B&B's new owner Matt, who bears an uncanny resemblance to the handsome hero from Izzi's novels. As both partake in the lodge's annual itinerary of Christmas activities, Izzi's writer's block is cured and the first pages of her and Matt's own love story may just be beginning.

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.

Times Square Playboy

A stock broker's small-town best friend thinks the bride-to-be and her family are gold-diggers so he does everything he can to prevent the wedding.

Three-Cornered Moon

Elizabeth Rimplegar inhabits a household populated by virtual lunatics. Her mother, Nellie, mishandled the family fortune, and, alas, the stock market crash has depleted their worth. Elizabeth's goofy brothers cannot easily adjust to the life of the average worker. Meanwhile, the family doctor has his eye on Elizabeth, but he will have to compete with her suitor, an ill-informed writer.

A Free Soul

An alcoholic lawyer who successfully defended a notorious gambler on a murder charge objects when his free-spirited daughter becomes romantically involved with him.

The Married Virgin

In order to save her wealthy father from disgrace and a possible prison sentence, a daughter agrees to marry the gigolo who's been blackmailing him...

Free and Easy

This MGM B-picture was adapted from Ivor Novello's play The Truth Game. Max and Florian Clemington pretend to be members of the landed gentry. Max romances the much-older Lady Joan Culver before finding true love in the form of pretty heiress Martha Gray.

Come Live with Me

Seeking US citizenship, a Viennese refugee arranges a marriage of convenience with a struggling writer.

The Rich Are Always with Us

A wealthy couple's marriage is falling apart due to the man's infidelity. The wife's male friend has long loved her and sees his big opportunity.

The Mysterious Mr. Valentine

Janet Spencer is driving down a country road when one of her tires blows out. This seemingly innocuous, everyday occurrence leads Linda into a labyrinth of murder, blackmail and intrigue.

Fall

For Michael Shiver, life as an easy-going cab driver in New York suddenly changes when he picks up supermodel Sarah Easton and falls head over heels in love. But Sarah has more than just passion on her mind; she also has a husband and a glamorous lifestyle that she can't seem to leave behind. Torn between her feelings for Michael and the security of her marriage, Sarah is forced to make a realistic decision about the sacrifices that must be made to be truly and totally in love.

Worth Winning

Taylor is a man who has no problems with women. So confident is he that he accepts a challenge from his friends: he has to secure proposals of marriage from three women of their choice.

The Affairs of Martha

Members of a well-to-do small community become worried when it is revealed that one of their maids is writing a telling exposé.

Devil-May-Care

A follower of Napoleon escapes the firing squad, flees to a woman's bedroom and winds up butler.

Man-Proof

A newspaper illustrator tries to remain best friends with the man she secretly loves, even though he recently married another woman.

Summer Villa

Although a successful romance novelist, Terry Russell hasn't had luck in her own love life. After a disastrous first date with cocky, hot-shot New York chef Matthew Everston, she retreats to her friend's French villa for the summer to finish her latest novel, with her reluctant teenage daughter in tow.

The World's Oldest Living Bridesmaid

A sophisticated lawyer (Donna Mills), who is always the bridesmaid but never the bride, gets romantically involved with her down-to-earth secretary (Brian Wimmer).

Personal Property

Raymond Dabney returns to his family after trouble with the law. He convinces the sheriff to give him a job watching the house and furniture of widow Crystal Wetherby without knowing she is engaged to his brother.

I Am the Edge

After a successful debut, novelist Sam Lamont (Jeremy Koerner) struggles to meet a looming deadline for his next book. Frustrated and desperate for inspiration, he begins to follow a mysterious drifter (Bill Olson) that appears in town. But when bodies start piling up and Sam's new muse proves to be more than just a harmless transient, his sanity and career are put in jeopardy as he goes on the run. Taking refuge with his family far from the city, it soon becomes clear to Sam that his stalker may have a deeper motive for his erratic behavior in this terrifying psychological thriller.

Lady of the Tropics

Playboy Bill Carey woos a half-caste beauty in French Indochina, but her second-class legal status makes a formidable barrier.

The Mistletoe Inn

When aspiring romance novelist Kim Rossi is unceremoniously dumped by her soon-to-be-published romance novelist boyfriend, Kim takes stock and decides to take a leap. She signs up for a romance writing retreat at a quaint Vermont Inn shortly before Christmas, where a top romance novelist is scheduled to attend and read the work of one lucky writer. Shortly after arriving, she crosses paths with Zeke, whom she initially finds to be intrusive and, naturally, ends up being her assignment partner. Worse yet, her ex is also at the retreat. Despite these bumps in the road, Kim steps outside her comfort zone and plunges into the writing exercises, surprising herself. Equally unexpected is the attraction that seems to be building between her and Zeke that promises to take her down a road she never imagined traveling. Based on the book by Richard Paul Evans.

It's All Yours

Jimmy Barnes arrives from Europe to be educated by his multi-millionaire uncle, Edward J. Barnes and in five years the extravagant escapes of Jimmy, now a lawyer, are the talk of San Francisco. Linda Gray is a mouse-like secretary to the elder Barnes who has fallen in love with Jimmy, but he favors actress Constance "Connie" Marlowe. Mr. Barnes dies and leaves everything to Linda but he has urged his partner, Alexander Duncan, to plan things so that Jimmy and Linda will get married. Coached by Duncan, Linda accepts the inheritance and announces that she is departing for New York on a wild spending spree. He tells Jimmy that the will can be broken but only after many months and he suggests that Jimmy follow Linda and curb her spending or there won't be any money left. In New York, Linda hires Jimmy as her private secretary. Connie also arrives in New York, as does the ingenious Baron Rene de Montigny with the intention of marrying the wealthy Miss Gray.

The Golden Arrow

A fake heiress marries a common reporter to thwart the advances of gold-digging playboys.

Perfect on Paper

Portland book editor Natalie Holland has chosen the wrong guy – another underachiever – once again. With her life going nowhere fast, she accepts a job offer from publisher and friend Avery Goldstein and moves to Los Angeles. A woman of depth and principle, Portland chic Natalie is a fish out of water in LA. Things only get worse when she learns she’s been hired to edit the latest romance novel from bestselling author Beverly Wilcox, a powerful, glamorous and intimidating figure straight out of "The Devil Wears Prada".

The Talk of the Town

Her strict upbringing is driving Genevra French (Dorothy Phillips) crazy, so when she gets her hand on a book called "How to Attract the Opposite Sex," she takes its advice to heart. She uses her newly found wiles on Lawrence Tabor (William Stowell) and gets him to marry her. Only after the wedding does she tell him she married him just to get away from her family, and that she intends to do exactly as she pleases.

Hold Your Man

Ruby falls in love with small-time con man Eddie. During a botched blackmail scheme, Eddie accidentally kills the man they were setting up. Eddie takes off and Ruby is sent to a reformatory for two years.

Dramatic School

Aspiring actress Louise Muban attends the prestigious Paris School of Drama during the day and works at a dreary factory assembling gas meters at night. She daydreams and "acts" her way through life, and her fellow students at school begin to suspect her stories are just that - fabrications. After Louise begins to weave an actual meeting with a debonair playboy into a fantasy of club dates and romance, her classmate Nana discovers the lie when she too meets the playboy. Nana sets a trap for Louise, and the result is an end to one fantasy and the realization of another.

Blonde Inspiration

A writer of pulp Westerns cranks out more words than his editor and publisher want to pay for.

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