Romantic Comedy films have seen many characters come and go. Some of these characters are extremely hopeful and giddy when it comes to the idea of true love. Other characters are driven to believe that the concept of “true love” is as mystical and fictional as the loch ness monster.
Let’s take a look at the ranking of rom coms’ biggest hopeless romantics to the biggest cynics from some of the biggest old school classics of all time to more recent modern hits.
10. GISELLE - ENCHANTED
Giselle is the ultimate advocate for true love. It’s practically all she ever thinks about. Her character is the definition of a hopeless romantic, albeit a satirical depiction of this type of character. Giselle takes a look at your average Disney Princess and places this archetype into the “real world”.
Despite the nitty-gritty elements of reality, Giselle never gives up on the idea of finding her true love. She doesn’t let the cynism of reality take away from her faith in the name of romance.
9. GIGI - HE’S JUST NOT THAT INTO YOU
Gigi, played by Ginnifer Goodwin, is a hopeless romantic in a world full of cynics. In the film, which is based on the book with the same title, Gigi never stops believing that she will one day find her soulmate. Even though everyone around her tells her to give up on this childish dream, she simply refuses to.
It gives audiences faith when we see how dedicated she is towards making herself happy by finding that special someone. It inspires us to never give up on love.
8. DOROTHY BOYD - JERRY MAGUIRE
Dorothy Boyd is the ultimate hopeless romantic in the 90s classic Jerry Maguire. Although she is a full-grown adult with an eight-year-old child and a husband who walked out on her, she is still a firm believer in love and she never gives up hope that she will one day have a happy ending with the man of her dreams.
It sounds totally cheesy, but it’s actually pretty inspiring to watch how this woman never gives up her faith in love, regardless of how difficult things get. She is such a hopeless romantic, that she invented the famous line, “You had me at hello.”
7. JAMIE RELLIS - FRIENDS WITH BENEFITS
Mila Kunis and Justin Timberlake star alongside each other in Friends With Benefits, which tackles the tricky topic of “casual sex”. It questions whether or not it is possible to share a bed with someone without catching feelings for them.
For Kunis and Timberlake, as it turns out, they can’t help but fall for one another. Cliche? Yes. Romantic? Most definitely. Kunis’s Jamie is unashamed to admit how much of hopeless romantic she is, and how even though she is an adult, she still craves that fairytale happily ever after. In the end, as expected, her wish comes true.
6. JO STOCKTON - FUNNY FACE
Audrey Hepburn plays Jo Stockon in the film Funny Face, where she stars alongside Fred Astaire as his love interest. Jo Stockon is a timid young woman who works at a bookstore and is often caught with her nose in a novel.
Her character is quite inexperienced when it comes to romance and dating, yet after she has her first kiss, she is a totally different person. A person who is filled with hope and wonder. A person who is thrilled to be alive. She even sings a beautiful love ballad called “How long has this been going on”, where she wonders how one simple kiss could “do all this”. It is most certainly worth a watch for all the hopeless romantics out there.
5. ROBBIE HART - THE WEDDING SINGER
Robbie Hart is the ultimate mixed bag in The Wedding Singer. Portrayed by Adam Sandler, one moment Robbie will be singing about how in love he is and how excited he is to finally get married, while in the next moment he’s giving a hateful performance with a song titled “Love Stinks”.
At some points in the film, he is the biggest hopeless romantic that we’ve seen, while in other sections he claims life would just be better if he stayed single forever. It sounds like how most of us feel when it comes to love, considering we all go through ups and downs in our romantic lives.
4. TOM HANSEN- 500 DAYS OF SUMMER
Tom Hansen may start off as the ultimate hopeless romantic, but that quickly changes after Summer, the love of his life, begins to pull away. After this, Joseph Gordon Levitt’s character becomes the total opposite of a hopeless romantic and he begins to despise anything that involves happiness or romance.
Coincidentally, one of the very first lines in the movie is, “this is not a love story.” It perfectly sums up Tom’s approach to love as the movie progresses, and as Summer slowly disappears from his life, so does his happiness.
3. MELVIN UDALL - AS GOOD AS IT GETS
Melvin Udall is cynical to a fault in the 80s romantic comedy As Good As It Gets. In the film, Udall plays a best selling romance novelist. Ironically, he is pretty much disgusted by the idea of all that mushy romance stuff and he seems to prefer being alone rather than finding a partner to spend the rest of his life with.
It isn’t until he gets close with Helen Hunt’s character, Carol Connelly, that he begins to accept the fact that love isn’t such a terrible thing after all. In fact, it is something that makes him incredibly happy and kinder.
2. HOLLY GOLIGHTLY - BREAKFAST AT TIFFANY’S
Holly Golightly, played by the elegantly iconic Audrey Hepburn, is a true cynic when it comes to love. She considers all of her past lovers to be her “rats” and because she is afraid to be caged in by love, Golightly only goes after men for their money.
In Holly’s eyes, being married to someone or tied to them in any way will stop her from being able to be free. Since Holly is such a free spirit, she is terrified of losing this freedom. In the final scene, she realizes that it’s okay to be vulnerable in love and she shares a passionate kiss in the rain while Moon River plays.
1. HARRY BURNS - WHEN HARRY MET SALLY
And finally, the award for the most cynical character in romantic comedy history goes to the one and only Harry Burns from When Harry Met Sally. Harry is not only cynical, but he’s actually proud of his cynicism and considers himself superior because of his “glass half empty” world view. When we are first introduced to his character at the beginning of the film, he drones on and on to Sally about his nihilistic world views and he makes it clear to her that he thinks this darkness inside of him trumps the happy go lucky mindset of people like Sally.
He wears his cynicism on his sleeve and faces many hurdles because of it, yet it isn’t until he almost loses his best friend Sally for good that he has a change of heart about love and romance. He begins to understand how beautiful it can be and how “when you realize you wanna spend the rest of your life with someone, you want that moment to start as soon as possible.”
