I think you will never go wrong with 'the classics' (but yes, depends on how you define it). But really, the classics are timeless. And whatever that may be -- a movie, a song, or a book, for it to be remembered after several years (or even decades, centuries), there has got to be (at least one) something special about it.
With that being said, Mark Steven Johnson's
When in Rome (2010) is obviously not a 'classic'. Bear with me, because the next one is.
Kristen Bell plays Beth Martin, a busy bee who may or may not be unlucky in love. Down and desperate, during her visit in Rome for her sister's wedding, Beth finds herself caught up in a crazy mess with several guys (stalking?) trying to win her heart after stealing coins from the Fountain of Love.

Nothing extraordinary about this one. Given your typical narrative, the only beautiful thing about this movie is
Veronica Mars finding true love in the perfect form possible — Josh Duhamel. And because of this pairing, the plot has somehow become tolerable, and (fine) entertaining enough to satisfy my
kilig craving. Still, the ending was awful. Rome was ethereal though.
So, yes. Here's a real classic. Gary Marshall's
Pretty Woman (1990). Julia Roberts as a hooker.
Edward Lewis (Richard Gere), a rich business man who needs a little time away from his busy life finds a beautiful hooker (Julia Roberts) to escort her in social events. Eventually, he falls in love with her.
Despite the really predictable story, Gere and Roberts simply have a certain kind of unforgettable chemistry that would make you want to watch this movie. Oblivious about the fact that Roberts plays a hooker here, I was in a bit of shock when I found out. Because seriously, she cannot pass as a prostitute (she just can't). Not that she did not give a remarkable performance (because she did, and that's actually 80 percent of the reason why
Pretty Woman is one of the most notable chick flicks of today), but because she was too classy. In my mind, she will always be that bubbly girl in
My Best Friend's Wedding. Playing as a hooker and still looking flawless. While Gere is simply charming. His eyes and smile is prince-like, making this Cinderella-story very fitting.
We all know that they would fall in love, and (yes) would end up together, yet their fist kiss appeared so magical. I guess, I'd have to give a point for that well-written screenplay.