1990s Rom-Com Couples We Still Wish Would Have Reunited for a Sequel

Anna and Will - Notting Hill

Picture Anna Scott walking back into William’s little bookstore years later, only this time with their child in tow. That alone would be enough to make fans smile. A sequel could explore how they balance fame, family, and everyday life while keeping their romance alive.

Joe and Kathleen - You've Got Mail

Remember when falling in love online felt like the biggest surprise ever? Joe and Kathleen's story still holds up beautifully. A follow-up could revisit their bookstore dreams, modern technology, and life as a long-term couple. It would also be fun to see how their playful rivalry has changed over the years.

Vivian and Edward - Pretty Woman

Vivian and Edward's fairy-tale ending left everyone wondering what happened next. A sequel might've shown how their relationship handled the real world after the romance settled down. Seeing Vivian continue to grow while Edward adjusted to a very different life would've created a special, emotional story.

Kat and Patrick - 10 Things I Hate About You

Yes, we all miss Heath Ledger, and beyond his Joker, this is the movie that we think about most. Let's jump ahead a couple of decades. Kat and Patrick have always marched to the beat of their own drum, so it would've been fascinating to see where life took them. A sequel could've explored careers, family, and whether they managed to keep their rebellious spirit alive.

Robbie Hart and Julia Sullivan - The Wedding Singer

One more song, anyone? Robbie and Julia could return in a sequel where they run a thriving event business while raising kids and adjusting to a changing world. New music, early internet culture, and plenty of wedding disasters would create the perfect backdrop for another feel-good adventure.

Julianne and Michael - My Best Friend's Wedding

Not every sequel needs to end with romance. Julianne and Michael's friendship was the real heart of the story, making a return feel especially exciting. With a new sequel already being developed, audiences could see them reconnect later in life while navigating new relationships, unexpected twists, or even divorce.

Cher and Josh - Clueless

As if fans wouldn't want another movie! Cher and Josh's relationship was sweet, funny, and surprisingly heartfelt. A sequel could catch up with them years later as middle-aged adults dealing with careers, marriage, and life beyond Beverly Hills. Alicia Silverstone and Paul Rudd remain incredibly popular, so bringing them back together would give longtime fans exactly the nostalgic reunion.

Charles and Carrie - Four Weddings and a Funeral

Believe it or not, Charles and Carrie still have plenty of story left to tell. Their romance survived endless twists before finally finding happiness together. A sequel could show what married life looks like after all those weddings, while revisiting the close-knit group of friends fans loved.

Josie and Sam - Never Been Kissed

Fast forward a few years, and imagine Josie looking back on her awkward undercover adventure with a smile. A sequel could explore how she and Sam built a life together while showing how much Josie has grown in confidence. Drew Barrymore's lovable energy mixed perfectly with Michael Vartan's charm, right?

Sam and Annie - Sleepless in Seattle

What happened after that magical meeting on top of the Empire State Building? That's the story fans have always wanted. A sequel could follow Sam, Annie, and Jonah as they build a family while proving that true love can survive everyday life, too. Tom Hanks and Meg Ryan created one of cinema's most unforgettable romances, and we are still not over it!