Best Romantic Comedies To Watch on Valentine’s Day

Valentine’s Day is very nearly here. For some, that might mean a fancy dinner at an expensive steakhouse and swapping equally expensive personal gifts. 

For others, that might mean simply getting a nice takeout meal and some cheap wine and having a good time with your partner, no matter the cost. 

For most, it likely entails watching a few lighthearted romantic comedy movies as a way to wrap up the special day.

Best Romantic Comedies To Watch on Valentine’s Day 

When Harry Met Sally…

When Harry Met Sally… tells the changing relationship between two fellow New Yorkers, Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan). Initially, the two meet on a long, cross-country trip from Chicago to New York shortly after college, though they part on less than amicable terms. 

You’ve Got Mail

As a general rule, pretty much any 1990s movie starring Tom Hanks opposite Meg Ryan is a romantic comedy worth seeing. The best and likely most wholesome would be their final collaboration together, 1998’s You’ve Got Mail. 

The Princess Bride

Adapted from William Goldman’s novel of the same name, Buttercup (Robin Wright) is a young woman betrothed to the power-hungry Prince Humperdinck (Chris Sarandon) in the fictional kingdom of Florin. 

The 40-Year-Old Virgin

Andy (Steve Carrell) is a good-natured, mild-mannered 40-year-old working at an electronics store. When his coworkers (Paul Rudd, Seth Rogen, and Romany Malco) discover that he hasn’t slept with a woman before, they try to help him lose his virginity.