The psychological complexities of two people joining together to form a couple have intrigued writers of all backgrounds throughout time. In modern day screenwriting, few movies have been more skilled at depicting the challenges of coupling than the romantic comedy When Harry Met Sally and the eccentric cult classic Harold and Maude.  The film When Harry Met Sally conveys to us that while it can be enormously rewarding, finding true love can also be difficult, confusing and complex. The narrative of When Harry Met Sally spans eleven years, taking its time to explore in often poignant and humorous ways, the many awkward stages that couples go through. In the dark comedy Harold and Maude, one of the most famous odd couples in movie history try to explore the meaning of life by understanding its beauty and simplicity. The film deals with the complications of what happens when two opposites meet and try to make a relationship work.

For Harry (Billy Crystal) and Sally (Meg Ryan) the road to becoming a couple is exceptionally arduous and complicated. As a testament to its genius the entire film focuses on the enormous resistances that two people have in becoming a couple. This is definitely not a story about love at first sight. It is obvious from the film that not all couples merge with the same intensity but nevertheless for Harry and Sally a desire for bonding exists. Ironically, both characters use sex as a way of avoiding their true intimate feelings. Harry believes that men and women can’t be friends because sex always gets in the way. Though talking in philosophical generalities, Harry is really talking about himself. It appears that Harry uses his desire to have sex as a way of avoiding his feelings. What we learn throughout the film is that whenever Harry has the opportunity to develop a romantic relationship with Sally his own fears about falling in love surface.

On the other hand, Sally states that men and women can be friends without having sex. She uses her philosophy to distance herself from her true feelings about Harry. Sally marries the man she thinks she loves because he meets the criteria of what she was taught to think love was. In reality she too is afraid to follow her heart because feelings of the heart are unpredictable and don’t always coincide with who she thinks she is. It is only when crisis hits Sally (the breakup of her marriage) that her true emotions finally overwhelm her. She allows herself to put her head and heart together by having sex with Harry. The rest of the film deals with the aftermath of their actions and tries to answer the question of how sex can alter a relationship. For Harry and Sally sex forced them do deal with the reality that they are truly in love. As with the “interviews” of elderly couples that are used throughout the film, Harry and Sally must recognize that their bonding has followed a unique and often circuitous route.

Unlike When Harry Met Sally, the story of two perfectly suited individuals, Harold and Maude tells the tale of two polar opposites both in age and philosophy.  Maude (Ruth Gordon) is everything Harold (Bud Cort) is not.  Harold is a depressed young man of nineteen completely disillusioned with life and deals with his need for attention and fulfillment by constantly staging his own suicide. His need for love is being side swept by his mother’s narcissistic concerns for herself. She attempts to find suitable marriage partners that she believes are appropriate for Harold, never recognizing that what he is longing for is the mothering he never received. It is not until he meets Maude does Harold begin to feel special. Maude teaches him to believe in himself no matter how odd and eccentric his beliefs may be and that finding true happiness in one’s life truly depends on the ability to be yourself. 

Harold on the other hand gives Maude what she truly needs at the end of her life, a sense of purpose. She sees in Harold the emptiness and disillusionment that she herself experienced. As a survivor of the Holocaust, Maude dealt with the inhumanity of life by learning to see the specialness in creation. That no matter what cruelty life threw at her, belief in the divine would overcome the pain.

By the end of the film we learn that true love is ultimately about respect. Harold must honor Maude’s desire to celebrate her eightieth birthday by allowing her to commit suicide. Unlike Harold’s adolescent suicide attempts, Maude has decided to end her life the way she planned it. She had made a commitment to herself that if she lived to be eighty that she didn’t want to die an ugly death but rather leave with grace and dignity. Though difficult for him to grasp, Harold does eventually realize that it was his love that allowed Maude to let go and follow the path that would give her the most inner peace. This realization becomes imbedded in his soul and we realize that Harold’s new sense of self, filled with courage, will allow him to lead a more fulfilling life.

Though stylistically different both When Harry Met Sally and Harold and Maude tell the story of individuals awkwardly struggling to find a way to bond and find strength in one another. Their journeys teach us that falling in love is never easy but rather filled with enormously complicated obstacles. That for every action one takes in the pursuit of love tremendous resistance will follow. That in finding true love one must first find the ability to find oneself.  For Harry and Sally it took eleven years of soul searching to finally come together and understand each other’s needs. For Harold and Maude it took the mutual recognition of each other’s emotional pain and a defiance of societal norms to allow them to fall in love