1. When Harry Met Sally (1989).
Everything about When Harry Met Sally is iconic, from the central question: can men and women just be friends? To the notorious café scene when Sally shows Harry that women can – and indeed do – fake orgasms.
2. Love Actually (2003)
With a dream of an ensamble cast including Emma Thompson, Liam Neeson, Kiera Knightley, and the late, great Allan Rickman this classic is about all different types of love, displayed with heart-melting sentimentality in the month before Christmas.
3. Notting Hill (1999)
Hugh Grant plays Will Thacker, atravel bookshop owner, who falls in love with Anna Scott, the biggest star in the world, played somewhat convincingly by Julia Roberts. The duo are cute and uncertain together, but shine best when around Will’s close-knit family.
4. It’s Complicated (2009)
Meryl Streep and Alec Baldwin play a middle-age couple who reignite the spark when they attend their son’s college graduation. The complicating factors? They’re divorced and he’s remarried.
5. Something’s Gotta Give (2003)
Jack Nicholson plays a senior citizen predatory music producer with a yen for younger women who falls in love with a woman closer to his own age. It’s intelligent and fun, and Amanda Peet electrifies the screen in the few moments she’s on.
6. His Girl Friday (1940)
A classic screwball comedy. Newspaper editor Cary Grant charms, coaxes, bullies, and uses every other trick in the book to keep his ace reporter ex-wife from remarrying. Will she go back to her ex or marry the dull as gravel new guy? With Cary Grant’s charm on full display, the answer is obvious – but it’s a rollicking good time watching them figure it out.
7. Pretty Woman (1990)
Julia Roberts plays a prostitute whose fortune changes when she meets a workaholic who needs an escort for social events. Despite the somewhat icky premise, it’s a classic for all the right reasons.
8. Roman Holiday (1953)
A tomboyish princess breaks away from her European tour to fall in love with a newspaper hack. The movie made Audrey Hepburn a star for good reason: it’s impossible to take your eyes off her.
9. Sleepless in Seattle (1993)
Tom Hanks plays a widower who moves with his son to Seattle to get a fresh start after his wife dies of cancer. On Christmas eve, eight -year old Jonah calls a radio show in an effort to find a partner for his dad. Meg Ryan and her pal, played by Rosie O’Donnell, conspire to meet the widower and through a series of near-misses and crazy coincidences, they eventually meet on top of the Empire State Building, and live happily ever after.
10. The 40 Year Old Virgin (2005)
Steve Carrell as the hapless, never-done-the-deed good guy is one of the most unique characters in cinematic history. He’s sweet and silly and when he meets a single mom, his heart is telling him this is the one while his body suffers from doubt. It’s sweeter than it’s given credit for, and it’s compulsively watchable.