Movies like With Love, Lilly (2003)
The best movies like With Love, Lilly (2003) are Love & Sex (2000), He Said, She Said (1991) and Walking and Talking (1996). If With Love, Lilly hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLove Don't Co$t a Thing (2003)7.7/10 from 742 votes
- NewestThe Best You Can (2025)Released 2025
Love & Sex (2000)
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHe Said, She Said (1991)
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisWalking and Talking (1996)
Just as Amelia thinks she's over her anxiety and insecurity, her best friend announces her engagement, bringing her anxiety and insecurity right back.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLove Don't Co$t a Thing (2003)
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisPeace, Love & Misunderstanding (2011)
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisAbout Love (2015)
What is love? The heroes of the film try to answer this question. A series of the most different characters and their stories are woven together. Small stories about various things, all about love: a young pair who prefer to live through images of Japanese anime-heroes; a secretary who receives an obscene offer from her boss; a Japanese woman who arrives in Moscow in search of a Russian man; a graffiti artist in search of beauty; an ex-wife employed by her husband for an unusual task; and many other things...
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisYou Will Meet a Tall Dark Stranger (2010)
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisPiter FM (2006)
Masha, who works for a radio station, and Maxim, a street sweeper with an architectural degree, cross paths with each other when they are at an indecisive point in their lives.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMuch Ado About Nothing (2011)
Two young lovers, Claudio and Hero, are to be married imminently but the devious scheming of a resentful Prince looks set to thwart the nuptials. Meanwhile, marriage seems inconceivable for reluctant lovers Beatrice and Benedick whose endless witty sparring threatens to keep them apart forever. Directed by Josie Rourke, Artistic Director of the Donmar Warehouse, Much Ado About Nothing is one of Shakespeare’s great plays and reminds us all of the failings and triumphs of the human condition in our never ending search for perfect love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Absolute CinemaMovies like thisSidewalks of New York (2001)
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCamille (2008)
A twisted honeymoon adventure about a young couple on their way to Niagara Falls.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMermaid (2007)
The fanciful tale of an introverted little girl who grows up believing she has the power to make wishes come true. She must reconcile this belief with reality when, as a young woman, she journeys to Moscow and grapples with love, modernity and materialism.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisDark Eyes (1987)
Aboard a ship early in the 20th-century, a middle-aged Italian tells his story of love to a Russian.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJust Before I Go (2015)
Ted Morgan has been treading water for most of his life. After his wife leaves him, Ted realizes he has nothing left to live for. Summoning the courage for one last act, Ted decides to go home and face the people he feels are responsible for creating the shell of a person he has become. But life is tricky. The more determined Ted is to confront his demons, to get closure, and to withdraw from his family, the more Ted is yanked into the chaos of their lives. So, when Ted Morgan decides to kill himself, he finds a reason to live.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCherry (2010)
Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJack Goes Boating (2010)
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMy Brilliant Career (1979)
A young woman who is determined to maintain her independence finds herself at odds with her family who wants her to tame her wild side and get married.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisAmerican Splendor (2003)
An original mix of fiction and reality illuminates the life of comic book hero everyman Harvey Pekar.
Why it matches: Similar story and style · both comedy & drama
Worth the HypeMovies like thisDamn Poverty! (2009)
Muhammad Yunus, Nobel Peace prize winner, is known in the whole world as the banker of the poor, because he pioneered and tested a funding system in Bangladesh: by lending little sums of money to the less well-off with no interest, and returning it by installments gained with their work, people are able to get free from extreme misery. Thus, what can happen if three boys, just graduated, who live in Naples, try to import this funding system that subverts every economic rule?
Why it matches: Similar story and style · both comedy & romance
Letter to America (1999)
Two friends from Odesa try to compose a video message to their pals, emigrants to the United States. One of them rents his apartment to a tricky girl who invents various excuses not to pay the rent. An exceptional story about people on the verge of despair who nonetheless manage to enjoy life, even if these joys are beyond good and evil.
Why it matches: Similar story and style · both comedy & drama
2071 - Horoscopes and Psychotropics (2021)
It is a feature film in development and research. It tells the story of a pharmacopornographic treatment imposed on a woman after an attempted suicide. But it is the year 2071 that an alternative comes to her.
Why it matches: Similar story and style · both comedy & drama
Lady Chatterley (2006)
After a crippling injury leaves her husband impotent, Lady Chatterly is torn between her love for her husband and her physical desires. With her husband's consent, she seeks out other means of fulfilling her needs.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisYOYO (2017)
Caroline can't stand that she is a virgin...and then the world ends. In post-apocalyptic LA, after a dust storm has wiped out the planet, she is convinced that Francis was sent as the man to pop her cherry. YOYO is a heartfelt, dark comedy about finding meaning in life, even when life ceases to exist.
Why it matches: Similar story and style · both comedy
Isolde (1989)
After librarian Isolde attempts suicide, she leaves her politician husband for a younger student with a dark past. Isolde's former husband, however, has something else in mind for the young man.
Why it matches: Similar story and style · both drama
Wings of Christmas (2013)
The film's protagonists get an opportunity to make a wish. Consequently, their lives take the path they themselves ordained. Several "coincidences" bring them everything they wanted and they have the chance to experience their wishes. We are not only responsible in our lives for everything that we do, but also for everything we say, we think and desire.
Why it matches: Similar story and style · both romance
That Lovely Girl (2014)
Moshe and Tami are a couple, Moshe is in his fifties and Tami is in her early twenties. They live together in a cruel and violent relationship, from which Tami seems unable to set herself free. Tami and Moshe are father and daughter...
Why it matches: Similar story and style · both drama
Across My Land (2017)
Father and son 'minutemen' patrol the American/Mexican border near their home in Nogales, Arizona.
Why it matches: Similar story and style · both drama
Like With Love, Lilly and something else?
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Frequently asked questions
What are the best movies like With Love, Lilly?
The closest matches to With Love, Lilly are Love & Sex (2000), He Said, She Said (1991) and Walking and Talking (1996). Below are 27 more, each with the reason it matches.
What should I watch after With Love, Lilly?
Start with Love & Sex (2000), the closest match to With Love, Lilly.
What is the highest-rated movie like With Love, Lilly?
Love Don't Co$t a Thing (2003), rated 7.7/10 by 742 TMDB users.
What is the newest movie like With Love, Lilly?
The Best You Can (2025) is the most recent release on this list.
How are movies similar to With Love, Lilly chosen?
First come films that Trakt’s viewers watch alongside With Love, Lilly, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.