There’s no doubt the 90s and early 2000s created some of the best Romantic Comedies. I haven’t seen them all, but I’ve seen more than my fair share. Here’s my top 10 (in no particular order):
- How To Lose a Guy in 10 Days (2003)
-
We’ve got Kate Hudson, Matthew McConaughey, and an adorable love story. Definitely my top 3, could watch a million times. What I would give to be Kate Hudson in New York City *sigh*.
- The Wedding Planner (2001)
-
Starring Jennifer Lopez and, you guessed it, Matthew McConaughey. Who doesn’t love a forbidden romance? Jennifer Lopez serves us Girl Boss realness while figuring out her love life.
- Two Weeks Notice (2002)
-
A strong-willed woman who doesn’t need a man (except maybe she wants one). It’s Sandra Bullock, Hugh Grant, and a good love story. Throw some environmental protests and a needy boss in there and you’ve got yourself a movie.
- The Proposal (2009)
-
We’ve got another Sandra Bullock on the list, this time with Ryan Reynolds. This green card marriage starts as strictly business, but where does it end? Somewhere in Alaska with Betty White.
- 10 Things I Hate About You (1999)
-
If you haven’t seen this one, you lived your teenage years wrong. With that classic sisters are complete opposites storyline, Julia Stiles is set with Heath Ledger so her younger sister can start dating. What more could you need besides high school, teen angst, and a girl falling in love?
- Picture Perfect (1997)
-
Our queen Jennifer Aniston shows us career-woman independence, but can’t figure out why she’s single. She lies to seem more stable, working her way up the ladder in her advertising job. When her “boyfriend” comes in to visit, her plan backfires.
- You’ve Got Mail (1998)
-
There’s plenty of AOL chat nostalgia in this one. Small bookstore owner meets Corporate chain store, but wait, there’s more. Meg Ryan and Tom Hanks both chase a dream up and down New York.
- He’s Just Not That Into You (2009)
-
So. Many. Characters. How are all these people somehow connected to each other in such a big city? Who knows? We get some truth served on a silver platter when it comes to men and dating, so make sure you take notes.
- Rumor Has It (2005)
-
Feeling like you don’t quite fit in with your tennis-playing family is one thing. Finding out there might be a scandal to explain it is another. We’ve got Shirley MacLaine spilling family tea to Jennifer Aniston who finds out her life just might be a movie.
- The Wedding Date (2004)
-
Young Dermot Mulroney plays a mysterious male escort, paid by Debra Messing as a date for her younger sister’s wedding. From ex-boyfriend drama to steamy shower scenes (of Mulroney) this movie is a wild ride.