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If you like this romcom, watch this older (and probably better) romcom

The Awful Truth
★★★★

Other comedies of remarriage include The Philadelphia Story, My Favorite Wife, The Palm Beach Story, Love Crazy, and their countless remakes. 

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Cactus Flower
★★★★

Cactus Flower was remade as the inferior Just Go With It.

Come Live with Me
★★★★

Similar elements include green card marriage, the publishing industry, and a grandmother who helps get the couple together. 

Down with Love
★★★★★

Down With Love is an affectionate parody of 50s/60s sex comedies, specifically Pillow Talk and Lover Come Back (both starring Doris/Rock/Tony) and Sex and the Single Girl. Tony Randall cameos in his final role. 

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His Girl Friday
★★★★★

A gender bent adaptation of The Front Page. Switching Channels is a direct remake. 

How to Lose a Guy in 10 Days
★★★½

A witty battle of the sexes with elements of comedies of remarriage, reminiscent of old Hollywood screwballs and sex comedies. 

The Hudsucker Proxy
★★★½

The Hudsucker Proxy is a pastiche of screwball comedies and the works of Frank Capra, referencing His Girl Friday, Meet John Doe, Mr. Deeds Goes to Town, Mr. Smith Goes to Washington, and It’s a Wonderful Life. There are also similarities to Metropolis, How to Succeed in Business Without Really Trying, and The Sweet Smell of Success

I Love You Again
★★★

Both romantic comedies feature chaotic couples falling in love again after cases of amnesia. 

I Married a Witch
★★★★

I Married a Witch inspired the Bewitched TV show. Bell, Book and Candle is also very similar. 

Intolerable Cruelty
★★★

Intolerable Cruelty is inspired by the comedy of remarriage subgenre that The Awful Truth is the pinnacle of. 

It Happened One Night
★★★★½

Inspired countless remakes and the blueprint for romantic comedies such as, Roman Holiday, It’s a Wonderful World, The Philadelphia Story, and Leap Year

Kiss Me Kate
★★★½

Based off of The Taming of the Shrew. Other notable adaptations of The Taming of the Shrew include Woman of the Year and Moonlighting’s Atomic Shakespeare.

Love Affair
★★★★

Love Affair was remade the same director, Leo McCarey as An Affair to , which is directly referenced throughout Sleepless in Seattle.