The Best Relationship Movies

Movies that stayed with me and some that taught me a lot. Break ups, comings together, why we choose who we choose, and the lessons we need to learn.
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1.
Definitely, Maybe (2008)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter. (112 mins.)
Director: Adam Brooks
“ About the twists and turns, uncertainties, and risks of love, and how they eventually lead you to the one. ” - Sandyspeaks
 
2.
Swingers (1996)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Wannabe actors become regulars in the stylish neo-lounge scene; Trent teaches his friend Mike the unwritten rules of the scene. (96 mins.)
Director: Doug Liman
“ The ultimate break up movie. ” - Sandyspeaks
 
3.
(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
“ Another ultimate break-up movie. ” - Sandyspeaks
 
4.
Groundhog Day (1993)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A weatherman finds himself inexplicably living the same day over and over again. (101 mins.)
Director: Harold Ramis
“ We keep making the same mistakes until we learn from them. ” - Sandyspeaks
 
5.
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
“ The stages of love. ” - Sandyspeaks
 
6.
Mr. Nobody (2009)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A boy stands on a station platform as a train is about to leave. Should he go with his mother or stay with his father? Infinite possibilities arise from this decision. As long as he doesn't choose, anything is possible. (141 mins.)
“ Three different girls, three different lives--the consequences of our choices. ” - Sandyspeaks
 
7.
A Lot Like Love (2005)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together... (107 mins.)
Director: Nigel Cole
 
8.
TiMER (2009)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
If a clock could count down to the moment you meet your soul mate, would you want to know? (99 mins.)
Director: Jac Schaeffer
“ Relax, you're going to meet the one. And it will never be as you expect. ” - Sandyspeaks
 
9.
When Harry Met Sally... (1989)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship. (96 mins.)
Director: Rob Reiner
 
10.
In Search of a Midnight Kiss (2007)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Broke and alone on New Year's Eve, Wilson just wants to spend the rest of a very bad year in bed. But, when his best friend convinces him to post a personal ad, he meets a woman bent on finding the right guy to be with at midnight. (90 mins.)
Director: Alex Holdridge
 
11.
Before Sunrise (1995)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A young man and woman meet on a train in Europe, and wind up spending one evening together in Vienna. Unfortunately, both know that this will probably be their only night together. (101 mins.)
 
12.
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
“ Take a chance. ” - Sandyspeaks
 
13.
A Lot Like Love (2005)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together... (107 mins.)
Director: Nigel Cole