10. "The Perfect Man" (2005)
This is a film where Hilary Duff plays matchmaker for her single mom, Jean. Holly (Duff) is tired of moving every time her mom gets dumped, so she creates a fake secret admirer for Jean. Holly ropes in her mom's colleague to pretend to be this Mr. Wonderful, and high jinks ensue. Flowers show up, romantic emails are exchanged, and eventually, Jean wants to meet him. What's a daughter to do?
9. "Win a Date with Tad Hamilton!" (2004)
What if you really could win a date with a hot celebrity? Rosalee, a small-town grocery clerk, does just that with Hollywood heartthrob Tad Hamilton. But Rosalee's coworker Pete secretly pines for her and isn't thrilled about her newfound fame. Tad, realizing that he's falling for Rosalee for real, decides to move to her small West Virginia town.
Yep, it's a true love triangle with Hollywood glamour sprinkled on top!
8. "Just My Luck" (2006)
Lindsay Lohan and Chris Pine – come on, what more could you ask for? Ashley (Lohan) is a career woman with insane good luck. Jake (Pine), on the other hand, is a struggling bowler-slash-band manager who's down on his luck. They kiss at a masquerade ball and swap luck!
Ashley goes through a series of hilarious catastrophes while Jake's band suddenly takes off. They realize what happened and try to reverse the luck-swap with another smooch.
7. "Something New" (2006)
Kenya, an uptight African-American accountant, is set up on a blind date with Brian, a free-spirited white landscaper. They clash at first, but then Brian is hired to landscape her new garden. Sparks fly between weeding and planting, but Kenya's friends and family aren't so sure about this match.
It's not just about finding love, but also breaking down some societal norms along the way.
6. "Music and Lyrics" (2007)
Hugh Grant and Drew Barrymore? I mean, come on, it's a match made in rom-com heaven. Alex, a washed-up '80s pop star, needs to write a hit song for a current pop sensation. Problem? He's great with melodies but awful with lyrics.
Enter Sophie (Barrymore), his plant lady with a knack for words. Together, they compose not just a hit song but also a romantic chemistry that's off the charts. But will the song get finished when old boyfriends and media scandals come into play?
5. "John Tucker Must Die" (2006)
Revenge is a dish best served funny and romantic – at least according to "John Tucker Must Die". When three high school girls discover they're all dating the same guy, John Tucker, they decide he's gotta pay. Enter the new girl, Kate, who they coach to be John's dream girl just so they can break his heart later. But of course, our girl Kate starts actually falling for John.
Will they carry out their plan, or will love get in the way?
4. "Definitely, Maybe" (2008)
Ryan Reynolds plays a dad, Will, who's in the middle of a divorce. His precocious daughter Maya demands to hear the story of how her parents met. The catch? Will changes the names and some facts, turning it into a mystery love story. Maya has to guess which of the three women becomes her mom.
It's like "How I Met Your Mother," but with way fewer seasons and more adorable daddy-daughter moments. And, of course, a much better ending – sorry for rubbing some salt in your wounds, HIMYM fans.
3. "In Her Shoes" (2005)
Maggie, played by Cameron Diaz, is a bit of a wild child, and her sister Rose (Toni Collette) is a serious lawyer. After Maggie sleeps with Rose's boyfriend – yikes – the sisters stop speaking. Maggie discovers they have a long-lost grandmother and goes to live with her in Florida. Rose visits and the two mend fences, but not without some new love interests popping into the picture.
It's complicated but oh-so-sweet.
2. "Elizabethtown" (2005)
Orlando Bloom as a romantic lead, y'all! He plays Drew, a shoe designer who just tanked his company $972 million. Just as he's contemplating suicide, he learns his father died. Yeah, our boy Orlando sure got is rough. He flies to Kentucky for the funeral and meets Claire, a flight attendant played by Kirsten Dunst. She takes an interest in him, and they share what can only be described as a magical road trip.
This is a story of failed plans and serendipity at its finest, as inspirational as they come.
1. "Penelope" (2006)
"Penelope" is a modern fairy tale. Christina Ricci plays Penelope, a rich girl cursed with a pig nose. The curse will only break when she's loved by one of her own kind. Enter Max (James McAvoy), a gambler paid to woo her. Of course, he ends up genuinely falling for her, pig nose and all. But can he break the curse? You'll have to watch to find out!