Top 45 Unconventional Romance Films

My personal favorite romantic films...I tend to relate better to the more offkey side of love. Feel free to suggest more titles, I have already added some of your recommendations after watching them.
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1.
(500) Days of Summer (2009)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An offbeat romantic comedy about a woman who doesn't believe true love exists, and the young man who falls for her. (95 mins.)
Director: Marc Webb
 
2.
The Go-Getter (2007)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
When his mother dies, a teenager takes a road-trip in a stolen car to find his long-lost brother. Along the way he discovers a profound connection with the car-owner and with himself as well. (93 mins.)
Director: Martin Hynes
 
3.
Eternal Sunshine of the Spotless Mind (2004)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
When their relationship turns sour, a couple undergoes a procedure to have each other erased from their memories. But it is only through the process of loss that they discover what they had to begin with. (108 mins.)
Director: Michel Gondry
 
4.
Good Dick (2008)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A look at the relationship between a lonely introverted girl and a young video store clerk vying for her attention. (86 mins.)
Director: Marianna Palka
 
5.
Secretary (2002)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one. (104 mins.)
 
6.
My Sassy Girl (2001)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
Based on a series of true stories posted by Ho-sik Kim on the Internet describing his relationship with his girlfriend... (123 mins.)
Director: Jae-young Kwak
“ (or the American version with Elisha Cuthbert--I enjoyed both, but in different ways.) ” - ladyiswear
 
7.
Away We Go (2009)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A couple who is expecting their first child travel around the U.S. in order to find a perfect place to start their family. Along the way, they have misadventures and find fresh connections with an assortment of relatives and old friends who just might help them discover "home" on their own terms for the first time. (98 mins.)
Director: Sam Mendes
 
8.
Garden State (2004)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A quietly troubled young man returns home for his mother's funeral after being estranged from his family for a decade. (102 mins.)
Director: Zach Braff
 
9.
Moulin Rouge! (2001)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A poet falls for a beautiful courtesan whom a jealous duke covets in this stylish musical, with music drawn from familiar 20th century sources. (127 mins.)
Director: Baz Luhrmann
 
10.
I'm a Cyborg, But That's OK (2006)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A girl who thinks she is a combat cyborg checks into a mental hospital, where she encounters other psychotics. Eventually, she falls for a man who thinks he can steal people's souls. (105 mins.)
Director: Chan-wook Park
 
11.
Benny & Joon (1993)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A mentally ill young woman finds her love in an eccentric man who models himself after Buster Keaton. (98 mins.)
 
12.
Once (2007)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A modern-day musical about a busker and an immigrant and their eventful week in Dublin, as they write, rehearse and record songs that tell their love story. (85 mins.)
Director: John Carney
 
13.
Punch-Drunk Love (2002)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A psychologically troubled novelty supplier is nudged towards a romance with an English woman, all the while being extorted by a phone-sex line run by a crooked mattress salesman, and purchasing stunning amounts of pudding. (95 mins.)
 
14.
Spanglish (2004)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A woman and her daughter emigrate from Mexico for a better life in America, where they start working for a family where the patriarch is a newly celebrated chef with an insecure wife. (131 mins.)
Director: James L. Brooks
 
15.
Waitress (2007)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness. (108 mins.)
Director: Adrienne Shelly
 
16.
Lars and the Real Girl (2007)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A delusional young man strikes up an unconventional relationship with a doll he finds on the Internet. (106 mins.)
Director: Craig Gillespie
 
17.
Adventureland (2009)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
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. (107 mins.)
Director: Greg Mottola
 
18.
Juno (2007)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Faced with an unplanned pregnancy, an offbeat young woman makes an unusual decision regarding her unborn child. (96 mins.)
Director: Jason Reitman
 
19.
Mozart and the Whale (2005)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A love story between two savants with Asperger's syndrome, a kind of autism, whose conditions sabotage their budding relationship. (94 mins.)
Director: Petter Næss
 
20.
Wristcutters: A Love Story (2006)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A film set in a strange afterlife way station that has been reserved for people who have committed suicide. (88 mins.)
Director: Goran Dukic
 
21.
Shopgirl (2005)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A film adaptation of Steve Martin's novel about a complex love triangle between a bored salesgirl, a wealthy businessman and an aimless young man. (106 mins.)
Director: Anand Tucker
 
22.
Amélie (2001)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
Amélie is an innocent and naive girl in Paris with her own sense of justice. She decides to help those around her and, along the way, discovers love. (122 mins.)
 
23.
Happy Accidents (2000)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Ruby Weaver has man trouble: she tries to fix them, so she's stuck herself with a string of losers. Her current lover... (110 mins.)
Director: Brad Anderson
 
24.
Monsoon Wedding (2001)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A stressed father, a bride-to-be with a secret, a smitten event planner, and relatives from around the world create much ado about the preparations for an arranged marriage in India. (114 mins.)
Director: Mira Nair
 
25.
Fur: An Imaginary Portrait of Diane Arbus (2006)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Turning her back on her wealthy, established family, Diane Arbus falls in love with Lionel Sweeney, an enigmatic mentor who introduces Arbus to the marginalized people who help her become one of the most revered photographers of the twentieth century. (122 mins.)
 
26.
Daydream Nation (2010)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A city girl who moves to a small town and becomes entangled in a love triangle between her high school teacher and a stoner classmate. (98 mins.)
 
27.
Crazy, Stupid, Love. (2011)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A middle-aged husband's life changes dramatically when his wife asks him for a divorce. He seeks to rediscover his manhood with the help of a newfound friend, Jacob, learning to pick up girls at bars. (118 mins.)
 
28.
Kiss Kiss Bang Bang (2005)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A murder mystery brings together a private eye, a struggling actress, and a thief masquerading as an actor. (103 mins.)
Director: Shane Black
 
29.
Russian Dolls (2005)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Five years after their summer together in Barcelona, Xavier, William, Wendy, Martine and Isabelle reunite. (125 mins.)
 
30.
Wild Target (2010)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A hitman tries to retire but a beautiful thief may change his plans. (98 mins.)
Director: Jonathan Lynn
 
31.
The Tiger and the Snow (2005)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A love-struck Italian poet is stuck in Iraq at the onset of an American invasion. (114 mins.)
Director: Roberto Benigni
 
32.
Annie Hall (1977)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
Neurotic New York comedian Alvy Singer falls in love with the ditzy Annie Hall. (93 mins.)
Director: Woody Allen
“ Of course. Classic. ” - ladyiswear
 
33.
Moonrise Kingdom (2012)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A pair of young lovers flee their New England town, which causes a local search party to fan out to find them. (94 mins.)
Director: Wes Anderson
“ Honestly, best Wes Anderson flick EVER. ” - ladyiswear
 
34.
Love Songs (2007)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A musical interpretation of three lovers living in Paris. (91 mins.)
 
35.
The Vicious Kind (2009)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A man tries to warn his brother away from the new girlfriend he brings home during Thanksgiving, but ends up becoming infatuated with her in the process. (92 mins.)
“ This isn't -exactly- a love story, but I felt like it needed to be here. ” - ladyiswear
 
36.
Love & Other Drugs (2010)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A young woman suffering from Parkinson's befriends a drug rep working for Pfizer in 1990s Pittsburgh. (112 mins.)
Director: Edward Zwick
“ Hot, hot, hot. ” - ladyiswear
 
37.
Hysteria (2011)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
The truth of how Mortimer Granville devised the invention of the first vibrator in the name of medical science. (100 mins.)
Director: Tanya Wexler
 
38.
Boys Don't Cry (1999)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Female-born Teena Brandon adopts his male identity of Brandon Teena and attempts to find himself and love in Nebraska. (118 mins.)
Director: Kimberly Peirce
“ Everyone should see this film, even though it will tear you apart. ” - ladyiswear
 
39.
Serious Moonlight (2009)
    1 2 3 4 5 6 7 8 9 10 5.4/10 X  
A high-powered attorney duct tapes her adulterous husband to the toilet ... right before their home is invaded by burglars. (81 mins.)
Director: Cheryl Hines
“ This is just messed up...really, really dark humor. ” - ladyiswear
 
40.
Scott Pilgrim vs. the World (2010)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Scott Pilgrim must defeat his new girlfriend's seven evil exes in order to win her heart. (112 mins.)
Director: Edgar Wright
 
41.
The Giant Mechanical Man (2012)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him. (94 mins.)
Director: Lee Kirk
 
42.
The Rebound (2009)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
In New York City, a single mom captivates her new neighbor, a much younger man. (95 mins.)
Director: Bart Freundlich
 
43.
Safety Not Guaranteed (2012)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Three magazine employees head out on an assignment to interview a guy who placed a classified advertisement seeking a companion for time travel. (86 mins.)
Director: Colin Trevorrow
 
44.
Groundhog Day (1993)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A weatherman finds himself living the same day over and over again. (101 mins.)
Director: Harold Ramis
 
45.
Warm Bodies (2013)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
After a highly unusual zombie saves a still-living girl from an attack, the two form a relationship that sets in motion events that might transform the entire lifeless world. (98 mins.)
Director: Jonathan Levine
 
46.
Silver Linings Playbook (2012)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
After a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own. (122 mins.)
 
47.
It Happened One Night (1934)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A spoiled heiress, running away from her family, is helped by a man who is actually a reporter in need of a story. (105 mins.)
Director: Frank Capra
 
48.
How to Steal a Million (1966)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Romantic comedy about a woman who must steal a statue from a Paris museum to help conceal her father's art forgeries, and the man who helps her. (123 mins.)
Director: William Wyler
 
49.
Breakfast at Tiffany's (1961)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A young New York socialite becomes interested in a young man who has moved into her apartment building. (115 mins.)
Director: Blake Edwards
 
50.
Drive (2011)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A mysterious Hollywood stuntman and mechanic moonlights as a getaway driver and finds himself trouble when he helps out his neighbor. (100 mins.)
 
51.
How Do You Know (2010)
    1 2 3 4 5 6 7 8 9 10 5.4/10 X  
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. (121 mins.)
Director: James L. Brooks