The ’90s movies really knew how to sell romance in a fun and dramatic way, but, of course, a lot of them were full of cheesy lines, overused tropes, and some messed-up situations involving a door in the middle of the Atlantic Ocean. Then again, all that manufactured drama and unique plot twists are exactly why we still love to rewatch these old gems.
Here are some iconic ’90s movie couples we still adore.
Josie and Sam in Never Been Kissed
In Never Been Kissed, Drew Barrymore plays Josie, a young copy editor who goes undercover at a high school, while Sam, played by Michael Vartan, just happens to be a kind, thoughtful English teacher. This relationship is obviously tough because of the teacher-student taboo, even though Josie is actually 25. The movie walks a very fine rom-com line, but Barrymore’s knows how to work a camera and pretty much charms her way through the story without making it weird. The big baseball-field kiss was extremely cheesy, but that’s kinda the point. Josie finally gets the romantic moment, and Sam, well, he’s just glad to be there.
Vivian and Edward in Pretty Woman
Few ’90s couples are as instantly recognizable as Vivian and Edward. Pretty Woman could have been a dry story about a wealthy businessman and a woman from a completely different world, but Julia Roberts and Richard Gere turned it into something special. Viv is funny, mouthy, and full of personality, while Edward is pretty much the opposite of that. Together, they soften each other, and it’s just incredibly enjoyable to see how they influence one another, no pun intended. The movie is a fairy tale, there’s no denying that, but Roberts and Gere sell that fairy tale so well that it became one of the defining romances of the 90s.
Kathleen and Joe in You’ve Got Mail
Kathleen and Joe meet online and slowly fall in love through raunchy messages, never realizing they already hate each other in real life. Kathleen owns a small bookstore, while Joe’s got that big family-owned bookstore extravaganza. Their love story faces several challenges. After all, he is the reason her little shop is about to go out of business. But by the time Kathleen realizes Joe and her mysterious online crush are the same person, the movie has already convinced us that these two were always meant to find each other.
Jack and Rose in Titanic
Some couples are unforgettable, but then there’s Jack and Rose. These two are basically cinematic royalty. Titanic gave us all a romance we will never forget. Jack is young, naive, and full of life, while Rose is rich and quite adventurous, trying to escape the future she doesn’t want. When they meet, it’s like time freezes and they’re the only ones on that accursed ship. Their romance is short, intense, and, well, you all know how it ends, but that’s why it stayed with people for all these years.
Cher and Josh in Clueless
Clueless may look like a teen comedy, but it has a surprisingly sweet slow-burn romance at its core. Cher is a popular fashion icon but, unfortunately, she also loves sticking her nose in everyone’s business. The beautiful thing about our boy Josh is that he’s not afraid to confront her and call her out, which makes their banter the best thing about the whole movie. They annoy each other, challenge each other, and somehow become better people through it. By the end, Cher and Josh feel like a real couple, and we love to see it.
Lucy and Jack in While You Were Sleeping
Lucy and Jack’s setup is easily one of the strangest rom-com plots, but the payoff in the end is oh so sweet. Lucy saves Peter from an accident, he falls into a coma, and his family thinks she is his fiancée. Instead of correcting them, Lucy gets pulled deeper into the classic rom-com shenanigans. Sandra Bullock makes Lucy so lonely and lovable that you’re immediately rooting for her. Then Jack enters the picture. Unlike Lucy’s fantasy version of Peter, Jack is real. He talks to her, notices her, cracks jokes, and slowly makes her fall in love with him. It’s a mess, but we just can’t get enough of it.
Dorothy and Jerry in Jerry Maguire
While Jerry is trying to rebuild his career after a huge meltdown, Dorothy is that one supportive colleague who believes in him so much that she decides to leave with him. They’re doing fine at first, but their relationship becomes complicated because of Jerry’s hot temper. The iconic ending of Jerry Maguire isn’t just about Jerry saying the right words but about him finally seeing Dorothy for who she was and understanding what she has meant to him. It’s like an emotional wake-up call more than it is a romantic fairy tale.
Will and Anna in Notting Hill
A shy London bookshop owner and a Hollywood superstar? How can you not root for them? Even though it’s a little unrealistic, such a match-up makes watching Will and Anna totally irresistible. Their relationship doesn’t crash from the start because Will sees beyond Anna’s facade and doesn’t care about the celebrity image. And for her, he’s just a quiet little corner somewhere in London. All those misunderstandings, paparazzi going nuts, and plenty of emotional hesitation make their chemistry so much more fun to watch. Will and Anna gave us one of the most memorable rom-com fantasies of the decade, and we’re eternally grateful for that.
