1. "Before Sunrise" (1995)
It all starts in Vienna with Jesse, an American guy, and Céline, a French woman, meeting on a train. Classic meet-cute, right, but soon, things get complicated. Jesse's got a flight back to the States the next morning, so what's left to do? Jesse and Céline decide to spend the night wandering around Vienna, talking about everything from love and death to their future.
There's no dramatic climax here, just two people genuinely connecting while the city sleeps. The film only grossed about $5.5 million but it's a cult classic now, and for good reason.
2. "Untamed Heart" (1993)
We've got Caroline, a waitress in Minneapolis, and Adam, a busboy who's a bit of an introvert – oh, and he's got a baboon heart. Yes, literally. After saving her from an assault, they start getting closer. They face hurdles, including Adam's fragile health and societal judgment, but they navigate through it all, hand in hand. You're gonna wanna cuddle up for this one.
3. "Living Out Loud" (1998)
Don't you just love it when two unlikely people hit it off? Meet Judith, a divorcee still in love with her ex, and Pat, a chronically underachieving elevator operator. Judith's comfortable life is shattered after her divorce, but her interaction with Pat, including an impromptu trip to a boxing match and dancing at a jazz club, brings the spark back to her life.
It's complicated, messy, and wonderfully human.
4. "Next Stop Wonderland" (1998)
Ever believe in destiny? Erin and Alan sure make you want to. Erin, a nurse, has just been dumped and is pushed by her mom into blind dating. Alan, an aspiring marine biologist, is another victim of a series of romantic mishaps. Their lives intersect at various points, unbeknownst to them, throughout the film – like, they both frequent the same aquarium. However, they don't officially meet until the very end.
5. "The Wings of the Dove" (1997)
Set in 1910 London, Kate Croy is in a bind. She's poor but in love with a journalist, Merton. Her wealthy Aunt Maude threatens to disown her if she continues the affair.
Enter Millie, a rich American dying of an unnamed disease. Kate hatches a plan: get Millie to fall for Merton so when she dies, her fortune can be inherited, thus enabling her and Merton to be together. Sounds easy, right? Wrong. Feelings get complicated real fast, as, well, they always do.
6. "Kissing a Fool" (1998)
Max is a womanizing sportscaster (played by David Schwimmer, a far cry from Ross Geller). His best bud is Jay, a writer. Max is engaged to a woman named Samantha but gets cold feet. So what's his solution? He asks Jay to hit on Samantha to test her loyalty. Lo and behold, Jay and Samantha actually connect. Awkward, right?
7. "Beautiful Girls" (1996)
Ever been to a high school reunion and wondered what could've been? Willie does exactly that. He's a pianist who returns to his small hometown for a reunion and starts reflecting on life and love. He's got a girlfriend, but he's drawn to a 13-year-old girl named Marty who is wise beyond her years.
Hold on, you got it all wrong, it's not creepy; it's more about the connection and understanding they share.
8. "Bed of Roses" (1996)
Lisa, a high-powered investment banker, receives a bouquet of roses from a secret admirer. Turns out it's Lewis, a guy who saw her crying in her office window and felt compelled to cheer her up. He's a florist, which, come on, is the perfect job for a rom-com, right? They both have past traumas but find solace in each other.
9. "Sliding Doors" (1998)
Helen, played by Gwyneth Paltrow, is a London PR exec who gets fired. The movie splits into two timelines: one where she catches her train home and finds her boyfriend cheating, and one where she misses it and remains blissfully unaware. In the first timeline, she dumps him, changes her look, and starts her own PR company. In the second, she stays with him but eventually uncovers the truth.
It's like watching two movies in one!
10. "Return to Me" (2000)
Yeah, I know, this one's technically from 2000, but let's squeeze it in anyway. Bob, a building contractor, loses his wife in a car accident. Little does he know, her heart is donated to Grace, a waitress in need of a transplant. They eventually meet and feel an inexplicable connection, not knowing the actual heart connection they share.