20 best movies like Undateable John (2019)

Desperate for a good story, a sex-addicted journalist throws himself into the world of high-class escorts when he starts following a Stanford-educated prostitute.

When their father passes away, four grown, world-weary siblings return to their childhood home and are requested -- with an admonition -- to stay there together for a week, along with their free-speaking mother and a collection of spouses, exes and might-have-beens. As the brothers and sisters re-examine their shared history and the status of each tattered relationship among those who know and love them best, they reconnect in hysterically funny and emotionally significant ways.

A washed up Vegas lounge singer, Jack Satin (Hamilton von Watts), has no money, no job, and delusional aspirations of fame. When Jack is forced to leave Vegas, he packs up his old Cadillac and hits the road for Atlantic City. But his car dies in the desert and Jack is left stranded in the small town of Lost Springs. There, Jack meets jazz legend turned mechanic, Doc Bishop (Robert Guillaume), who helps him with his car trouble. Although Jack is far from the stage, he begins to find himself feeling at home in the small town. When he meets local bar owner, Lauren Wells (Melissa Joan Hart), Jack starts to see there is more to life than chasing fame and fortune. Doc encourages Jack to explore his true love of music, while Lauren provides the audience he has always wanted. But as Jack realizes this town has more to offer him than the bright lights of the big city, his Vegas past catches up with him -- what unfolds is comedy at the crossroads of life.

A man's (Hugh Laurie) affair with his friend's much-younger daughter (Leighton Meester) throws two neighboring families into turmoil.

Four lovers find themselves caught in a tangle of intersecting relationships in this engaging, New York-set romantic drama that explores the ripple effects of love and obsession.

Family friends Sam and Kat spend every Christmas Eve at the Children's Table. They grow up together, sharing the highs and lows of young adulthood. And at thirty, Sam realizes that Kat is the one...but he's afraid that the past will get in the way.

After getting his heart broken by his childhood sweetheart, Tom Campbell escaped from his home town to join the military. Years later, Tom returns home with the news of his grandmother’s failing health and business. A town treasure, Cupid’s is known for its enchanting reputation of guiding guests to find love. Chelsea, the mayor and Tom’s ex-flame, takes advantage of this bad news and devises a scheme to get the property sold to make way for a mall. Although pressured to save the bed and breakfast, Tom’s history of heart break makes it difficult to stand up for such a symbol of love. Sharing in his skepticism of love is Nancy, a new police officer in town. With Nancy’s encouragement, Tom just might make the effort to keep the landmark afloat after all.

Rebellious Mickey and good-natured Gus navigate the thrills and agonies of modern relationships.

As an asteroid nears Earth, a man finds himself alone after his wife leaves in a panic. He decides to take a road trip to reunite with his high school sweetheart. Accompanying him is a neighbor who inadvertently puts a wrench in his plan.

After false reports of his demise put him and his work on the map, an artist decides to continue the charade by posing as his own brother. Soon, a reporter enters his life and has a profound effect on him.

When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.

A couple who have known each other since 8 are destined to be together until death do them apart.

An aspiring fashion designer falls in love with her socialite client's prospective fiance, Prince Jeffrey.

Explores the early events leading up to Red Dog's discovery on the road to Dampier, and his ultimate rise from ordinary dog to Australian legend.

On the brink of separation, Ethan and Sophie escape to a beautiful vacation house for a weekend getaway in an attempt to save their marriage. What begins as a romantic and fun retreat soon becomes surreal, when an unexpected discovery forces the two to examine themselves, their relationship, and their future.

A seemingly perfect family moves into a suburban neighborhood, but when it comes to the truth as to why they're living there, they don't exactly come clean with their neighbors.

Two single friends agree to be each others' respective plus one for each wedding they're invited to during a particularly busy nuptial period of their lives.

The continuing adventures of the Portokalos family. A follow-up to the 2002 comedy, "My Big Fat Greek Wedding."

After his sudden firing, a popular radio DJ moves in with his aunt, bringing along his four spoiled children, and a plan to return to the airwaves.

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.

A self-centered realtor enlists the help of his neighbor when he's suddenly left in charge of the granddaughter he never knew existed until his estranged son drops her off at his home.

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.

Passions re-ignite and secrets revealed when a graphic designer reconnects with the great, lost love of his life for a weekend tryst at a house in the desert near Joshua Tree.

A coming of age story about a washed up twenty something year old, the onetime hometown hero and track star, who is convinced by a local sweetheart to run a marathon and get his life back on track.

Big city girls Julia and her best friend Sydney take a trip to a dude ranch in Wyoming for a fun weekend getaway, but after a brawl at the local bar, the girls are sentenced to stay in town and perform community service. Along the way, Julia finds love and her true calling in life.

A woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.

Dear Sidewalk tells the story of Gardner, a 24 year old mail-carrier, who is struggling to contend with his identity as his quarter-life crisis is in full swing. His regimented routine is thrown out the window when he meets Paige, a divorcee, enduring a mid-life crisis of her own. In this relationship there exists a synchronicity, as they find, despite their age difference, they're both confronting existential problems surrounding identity, love, and the choices in front of them.