Off the top of my head and stealing from IMDB Valentines Lists, here are some Valentines movies for various age groups/categories.
Beauty and the Beast
Better Disney animated movie with a smart female protaganist who Likes To Read and male who has an actual character arc.
Plot: Beauty and the Beast, y’all.
Sleepless in Seattle
You’ve Got Mail
People: Tom Hanks and Meg Ryan.
Sleepless in Seattle is a bit sharper when it focuses on Tom Hanks’ grief about his wife. You’ve Got Mail is straight up PLEASANT. No hard feelings, no tough arguments, no … unpleasantness. There’s a great line in Undeclared where the Seth Rogen character says describes it as warm water lapping up on your legs on the beach. Cozy. Both are well-written, though.
Plot: Attractive pleasant people wonder about love and feelings.
One Fine Day
People: George Clooney and Michelle Pfeiffer
Well written and fun, both characters are pretty smart and it’s nice to see a movie where George Clooney’s looks are used as a plot point.
Plot: Attractive single parents who miss a field trip and have to swap babysitting.
Catch and Release
People: Jennifer Garner and Timothy Olyphant
Roeper described this as the romantic comedy where people aren’t stupid and do what you think they might, and even peripheral characters have some depth.
Plot: Attractive lady mourns fiance and meets attractive friend who comes to his funeral where feelings occur.
Pretty sturdy romantic comedy that uses pies as a metaphor for a waitresses’ feelings.
Plot: Keri Russel (Felicity, that one 90s NYC romantic drama produced by JJ Abrams) is preggers, Nathan Fillion (neo Han Solo) is a doctor, feelings occur.
Out of Sight
People: George Clooney and Jennifer Lopez
Steven Soderbergh being awesome, using visual tonal shifts and kooky editing. It’s actually a heist caper movie but the romantic plot is great. From an Elmore Leonard book.
Plot: Attractive prisoner breaking out grabs an attractive cop by mistake and feelings occur.
People: Joanquin Pheonix, Scarlet Johansson’s voice.
More philosophical than pleasant but still a straightforward romantic drama.
Plot: Guy dates his OS.
The Philadephia Story (1940)
People: Cary Grant, Katharine Hepburn, James Stewart
Funny movie based on a play. Way funner to watch than it should be.
Plot: Attractive ex-husband shows up to attractive ex-wife’s funeral, feelings occur.
An Affair to Remember
People: Cary Grant and Deborah Kerr
It makes my mom cry.
Plot: Attractive people fall in love and agree to meet later and have trouble with it.
People: Ernest Borgnine, Betsy Blair
Movie about medium-looking people and how they might have feelings. It’s really good and won a bunch of awards.
Plot: See above.