(500) Days of Summer (2009)
What it’s about and why you should watch it for Valentine’s Day: Tom looks back on 500 days with Summer, the girl he’s sure is “the one,” in a nonlinear story that focuses on their relationship and how it falls apart. Perfect if you don’t want a cheesy fairytale. It’s about expectations vs reality and learning from heartbreak, so it’s great for self-reflection, watching with friends, or a “we survived our messy eras” date.
Eternity (2025)
What it’s about and why you should watch it for Valentine’s Day: In a whimsical afterlife, Joan has one week to decide where to spend eternity and with which man: the husband she spent her life with, or the first love who died young and has waited for her. It’s a very realistic movie about how some people are never over their first love, while some people prefer peace and stability over fleeting emotional attachment.
Mr. & Mrs. Smith (2005)
What it’s about and why you should watch it for Valentine’s Day: A bored married couple in suburbia discover they’re both secretly elite assassins working for rival agencies and are ordered to kill each other, which weirdly rekindles their marriage. Action and romance make for chaotic banter. Ideal if you want something fun and explosive (literally) that’s more “hot married people working on communication issues” than soft crying.
13 Going on 30 (2004)
What it’s about and why you should watch it for Valentine’s Day: After a disastrous thirteenth birthday, Jenna wishes to be “30, flirty, and thriving” and wakes up as a 30-year-old magazine editor. As she goes about her day, she has to piece together what she did with her life and what (and who) she really cares about. Soft, nostalgic, and cozy, it’s about second chances, childhood crushes, and becoming the kind of adult your younger self would actually be proud of.
The Notebook (2004)
What it’s about and why you should watch it for Valentine’s Day: In a nursing home, an elderly man reads a notebook telling the story of Noah and Allie, whose 1940s summer romance is torn apart by class differences and family pressure but never fully fades. Peak “sob into a pillow” Valentine’s classic. If you want a big, sweeping, dramatic love and a guaranteed cry, this is it.
La La Land (2016)
What it’s about and why you should watch it for Valentine’s Day: In L.A., aspiring actress Mia and jazz pianist Sebastian fall in love while chasing their dreams. Unfortunately for them, success forces them to make choices that pull them apart. It’s dreamy, colorful, and romantic but bittersweet. Ideal for “we love art, we love vibes, and we’re okay with a not-Disney ending.”
10 Things I Hate About You (1999)
What it’s about and why you should watch it for Valentine’s Day: At Padua High, Bianca can’t date until her antisocial older sister Kat does. A scheme is hatched to pay “bad boy” Patrick to take Kat out, but real feelings start to become involved. This movie has it all: iconic teen romcom energy, enemies-to-lovers, banter and one of the best grand gestures ever. Great if you want something fun and flirty with big 90s/00s vibes.
50 First Dates (2004)
What it’s about and why you should watch it for Valentine’s Day: Henry, a laid-back marine vet in Hawaii, falls for Lucy, who has short-term memory loss after a car accident. Every night, her memory resets, so she wakes up each morning thinking it’s the same day. Instead of giving up, Henry decides to make her fall in love with him every single day, coming up with new, creative “first dates” to win her heart over and over. It’s a fantastic rom-com classic that makes you believe in true love
Photo by Felipe Bustillo via Unsplash
