Rory teases Dean that one of his embarrassing secrets must be that the theme music to Ice Castles makes him cry. In turn, Lorelai counters that at the end of The Way We Were, he wanted Robert Redford to dump his wife and kid for Barbra Streisand.
Ice Castles is a 1978 romantic drama film directed by Donald Wrye, and with Lynne-Holly Johnson and Robby Benson in the lead roles. Highly sentimental, it’s about a young figure skater named Lexie who rises to stardom before a tragic accident robs her of her eyesight. With the help of her former boyfriend Nick, she learns to skate competitively even without normal eyesight, as they re-kindle their relationship. The theme song is Through the Eyes of Love, performed by Melissa Manchester.
The Way We Were is a 1973 romantic drama film directed by Sydney Pollack, and with Barbra Streisand and Robert Redford in the lead roles. The story takes place from the 1930s to the 1950s, and is about the relationship between two very different people: Katie is a Marxist Jew with strong anti-war convictions, while Hubbell is a handsome WASP with writing talent, but no strong work ethic or political opinions. Katie and Hubbell fall in love, marry, and have a daughter together, but they are too different for their relationship to last.
At the end of the movie they meet by chance some years after their divorce; Katie has remarried to a Jewish man, and Hubbell has a beautiful girlfriend (despite Lorelai’s recollection, it is Katie who is married with a child, not Hubbell). They share a tender moment together, but too much time has passed, and it is is apparent that love alone is not enough to make their relationship ever work. The Way We Were was the #5 movie of 1973 and won Academy Awards for its musical score and theme song. It is considered to be one of the greatest romantic films of all time.
I think it is not going too far to say that Rory and Lorelai have actually named their own favourite romantic tearjerkers. The films they have chosen reveal quite a bit about their attitude to romance and relationships.
Ice Castles is about a talented sixteen-year-old girl from a small town who is determined to make it to the top of her field, and works hard to get there. Even when fate hands Lexie a cruel blow, she is able to rise above it and overcome her problems. Her boyfriend Nick basically exists in the plot just to encourage her, and to push her to succeed in reaching her goals. Lexie is unfaithful to Nick with an older man, but he is able to forgive her and begin their relationship anew.
I suspect Rory sees Lexie as something to aspire to, and that she understands her sense of driving ambition (Rory starts late at Chilton, just as Lexie comes into the world of competitive skating at a later age than usual). Both are working hard to catch up, and determined to succeed. Not having any relationship experience, her romantic fantasy is one where she can sexually experiment and be forgiven for it, and have a partner who is her support system and makes her dreams his own. The film’s setting in the snow and ice of winter suggests Rory’s virgin status.
The Way We Were has major parallels with Lorelai’s own life. Like Katie, she is a quirky and opinionated character, and Katie’s attraction to the handsome, privileged Hubbell reminds us of Lorelai’s relationship with Christopher – like Katie and Hubbell, Lorelai and Christopher were friends before they were lovers.
Katie and Hubbell separated when their daughter Rachel was born, as a parallel to Lorelai and Christopher breaking up after the birth of Rory. Like Hubbell, Christopher has gone to live in California and is not part of his daughter’s life. Just like Katie with Hubbell, Lorelai still has feelings for Christopher, but recognises that he is weak and lazy, and that their relationship could not work long term. She will not compromise herself to be with a man, even one she cares for.
That this movie has such a deep fascination for Lorelai is a reminder that her teenage relationship with Christopher is not just the great romance of her life, but her only real romance. Unlike Katie, she has not been able to move on and find someone else, so that she is emotionally stuck.
Lorelai is stunned to discover that Dean has never seen The Way We Were (because most teenage boys love Barbra Streisand movies), and decides that they will watch it for their next pizza-and-movie night. Dean is obviously completely smitten with Rory, because he agrees to this.