When I decided to make a list of my top five romantic comedies I realized I'd HAVE to break this list up into classic movies and modern movies because there was just no way to narrow it down to five otherwise. As a classic film fan, it's actually going to be even harder to pick just five pre-'80s films but I can cross that bridge when I get to it. Today I'm just talking about modern (1990-present) movies -- in no particular order.
Never Been Kissed (1999) As long-time readers already know, I've been single for my entire life and I've never even been on a date. I've come to terms with it in the last couple years and I'm pretty happy and contended settling into a life of certain spinsterhood but for most of my teens and 20's I would SO live vicariously through this movie, and even now I root so hard for Josie.
Return To Me (2000) This is my favorite modern romantic comedy, and I think it's criminally underrated. It takes what could have been a really uncomfortable, tragic hook and turns it into an incredibly sweet and charming movie. The supporting cast is perfect, and David Duchovny and Minnie Driver are the most adorable couple of all time. This movie is so heartfelt and sincere and just absolutely lovely.
You've Got Mail (1998) It says a lot about how much I love this movie that there are elements to the plot that annoy me SO much and I still rewatch it at least once or twice a year. It's so endlessly quotable, the seasons are so vivid (I always think of it as a fall/winter movie but the spring scenes are just so spring-y, too!) and it just doesn't get better than Meg Ryan and Tom Hanks (except maybe David Duchovny and Minnie Driver, lol!) Also I just support any movie that involves Greg Kinnear.
Music and Lyrics (2007) I just discovered this one recently and fell so head over heels for it that I watched it twice in the same day. Hugh Grant plays a fallen pop idol and the songs from his fictional 80s band are so insanely catchy. Plus his chemistry with Drew Barrymore is fantastic and even though the movie dips into "stahpppp, just talk to each other and sort things out!!!" territory at one point I wasn't even mad because the whole thing is just so adorable.
Romantics Anonymous (2010) This French film is about two incredibly, painfully shy people who start dating and all of the anxiety and setbacks they go through to make it work. As a introvert on the level of Hermit, I related to this movie so much and it was such a joy to watch a romantic pairing that wasn't easy and casual and laid back. The comedy is even funnier if you're super shy yourself because you can imagine EXACTLY what the characters are going through and how awkward and bumbling their situations are. Even if you're an extrovert, though, I highly recommend it. It's super sweet (it involves chocolate, so I mean that literally and figuratively!)
