Romantic Movies to Watch on New Year’s Day

Rob Reiner once mentioned something on The Drew Barrymore Show that I couldn’t stop thinking about. Some fans of his 1989 movie deliberately start it at 10:30 p.m. on New Year’s Eve so that the final scene lands right around the real midnight countdown. That’s a pretty serious level of movie commitment, but honestly, I get it. A few films become part of people’s traditions in ways you never expect.

For this list, I picked five romantic movies from different decades, with very different moods. I also wanted more than the usual plot summaries, so each one has a story, bit of trivia, or behind-the-scenes detail that makes it a little more interesting to watch. You’ll also find the rating, genre, and runtime for each. And don’t worry, there are no ending spoilers.

When Harry Met Sally, 1989

Billy Crystal and Meg Ryan spend almost a decade moving in and out of each other’s lives in this one. They first meet as strangers on a road trip, become friends somewhat reluctantly, and eventually find themselves wondering whether their friendship might actually be something more. Nora Ephron wrote the screenplay, Rob Reiner directed it, and the movie runs for 96 minutes. It’s rated R and still has an impressive 7.7 IMDb rating, which says a lot considering it’s been around since 1989.

The detail I keep coming back to isn’t really about the plot. Ilana Kaplan, author of Nora Ephron at the Movies, discussed the movie on NPR’s It’s Been a Minute around New Year’s and made an interesting point: When Harry Met Sally helped turn New Year’s Eve into the perfect setting for a romantic comedy. Plenty of movies have borrowed that idea since.

Then there’s the Princess Diana story. The movie premiered in London in 1989, with Diana among the audience. Billy Crystal joked that if she took off her shoes during the screening, he would take off his pants. She apparently found the whole thing hilarious and later asked Rob Reiner for a VHS copy so she could watch the movie again with friends.

R | Comedy, Drama, Romance | 7.7/10 on IMDb | 96 minutes

Serendipity, 2001

John Cusack and Kate Beckinsale meet over the same pair of gloves at Bloomingdale’s one December evening. There’s just one problem: they’re both already dating other people. They spend a few hours together in Manhattan, hit it off, and then make a pretty wild decision. Instead of simply exchanging phone numbers, they leave their future to fate.

He writes his number on a five-dollar bill. She writes hers inside a book and sends it off to a used bookstore. Then they go their separate ways and let the universe figure out the rest.

Nell Minow of Common Sense Media described it as a “lightweight romance” that “may appeal to teens,” giving it four out of five stars. That’s probably the right way to look at it. Serendipity isn’t trying to change your life or make some huge statement about love. It’s a sweet, easy movie that knows exactly what kind of evening it belongs to.

There’s also a surprisingly significant piece of movie history hiding in the background. The film was shot in New York before September 11, 2001, which meant the World Trade Center towers appeared in its skyline footage. After the attacks, the towers were digitally removed before the movie’s October release. If you’ve watched Serendipity recently, you might never have realized those shots were changed.

PG-13 | Comedy, Romance | 6.8/10 on IMDb | 91 minutes

Bridget Jones’s Diary, 2001

This is probably the most fitting choice if you’re actually watching on January 1. The movie begins on New Year’s Day, with Bridget deciding that she’s going to take control of her life. Naturally, that means starting a diary and keeping track of things like cigarettes, calories, and all the habits she’s determined to change.

What follows is a wonderfully messy romantic triangle involving her attractive but questionable boss and Mark Darcy, a much more reserved family acquaintance. I won’t get into where it goes, but if you’ve somehow managed to avoid this movie for nearly 25 years, it still holds up surprisingly well.

The opening scene is one of the movie’s most memorable moments. Bridget is alone in her apartment, drinking and singing along to a sad song while wearing pajamas. It’s awkward, funny, and painfully relatable, which is probably why the scene has stuck around for so long.

Here’s a bit of trivia I hadn’t known: Bridget Jones’s Diary opened at number one at the UK box office, earning more than £5.7 million in its first weekend. At the time, that made it the biggest opening ever for a British-made film.

And Mark Darcy’s name is very much intentional. He’s a nod to Mr. Darcy from Pride and Prejudice. Casting Colin Firth made the joke even better because he’d already played Mr. Darcy in the BBC’s Pride and Prejudice just six years earlier.

R | Comedy, Romance | approximately 6.7/10 on IMDb | 97 minutes

New Year’s Eve, 2011

Let’s be honest about this one before you start it. Garry Marshall packed an almost ridiculous number of recognizable actors into one New Year’s Eve in New York. Robert De Niro, Halle Berry, Zac Efron, Michelle Pfeiffer, Ashton Kutcher, Sarah Jessica Parker, and plenty of others each get their own storyline, with everything eventually connecting around the Times Square ball drop.

It’s basically a bunch of little romantic dramas happening at the same time rather than one traditional story.

Critics were not kind to it. Peter Travers of Rolling Stone gave it zero stars and called it “bad beyond belief.” Mark Kermode named it the worst film of 2011, while Claudia Winkleman said on the BBC’s Film show, “I have found the worst film of all time, and it is called New Year’s Eve.” So, yeah. The reviews were not exactly subtle.

But Owen Gleiberman of Entertainment Weekly had a much more forgiving take. He called it “dunderheaded kitsch” but also described it as the sort of holiday movie that can “sweetly soak up a holiday evening.” Honestly, that’s probably the best way to sell it.

It’s not a masterpiece. It doesn’t need to be. If you’re watching with friends, eating popcorn, and looking for something easy that keeps the holiday atmosphere going, it can be surprisingly enjoyable. The box office certainly wasn’t terrible either. The movie made around $142 million worldwide against a reported $56 million budget.

PG-13 | Comedy, Romance | approximately 5.7/10 on IMDb | 118 minutes

About Time, 2013

Save this one for when you want something more than a cute romance. About Time starts with a pretty incredible premise. On his 21st birthday, Tim discovers that the men in his family can travel back through their own lives. They can’t change other people’s timelines, but they can go back and experience their own moments again.

Naturally, Tim initially uses the ability for the most obvious reason possible: trying to get better at talking to a woman he likes. But the movie gradually becomes much bigger than its romantic storyline. It starts asking questions about family, time, regret, and whether we’re actually paying attention to the ordinary days we’re living.

Richard Curtis wrote and directed the film, so the emotional side shouldn’t come as a surprise. He’s also behind Love Actually and Notting Hill. Curtis has talked about how becoming a father made him think about the ordinary moments he’d want to experience again if he could. That idea shows up throughout About Time, especially in the quiet family scenes rather than the big romantic ones.

There’s one detail that gives the movie an extra emotional weight. It’s dedicated to actor Richard Griffiths, who appears in a supporting role and died in March 2013, several months before the film was released that November. The dedication is easy to miss if you’re not paying attention to the credits, but it feels especially fitting for a movie so focused on how little time we actually get with the people we love.

R in the US, 12A in the UK | Romance, Comedy, Drama, Fantasy | 7.8/10 on IMDb | 123 minutes

Where They Stand, Side by Side

So Which One Tonight

If you want the movie that has actually become part of people’s New Year’s traditions, go with When Harry Met Sally and try the 10:30 p.m. start so the ending lines up with midnight. Want something shorter and easy to watch? Serendipity is a good choice and doesn’t demand much from you.

If you’re watching on January 1 itself, Bridget Jones’s Diary is almost suspiciously perfect for the occasion. Watching with a group of friends? New Year’s Eve works better when everyone is there to laugh at the ridiculousness together. And if you’re in the mood for something that starts as a romance but leaves you thinking about your own life afterward, choose About Time.

Frequently Asked Questions

Which of these has the highest IMDb rating?

About Time currently leads the group at 7.8, followed closely by When Harry Met Sally at 7.7.

Is New Year’s Eve actually as bad as critics say?

Some critics were absolutely ruthless about it. Peter Travers and Claudia Winkleman were particularly harsh, while others found some charm in its deliberately cheesy holiday style. If you expect a serious romantic drama, you’ll probably hate it. If you want easy holiday entertainment, it may work surprisingly well.

Which movie is appropriate for teenagers?

Serendipity and New Year’s Eve are both rated PG-13, making them the two more teen-friendly choices on this list.

Is When Harry Met Sally actually set on New Year’s Eve the whole time?

No. The movie follows Harry and Sally across roughly a decade, with the story eventually arriving at a New Year’s Eve celebration for its final scene.

Why does Bridget Jones’s Diary open on January 1st specifically?

New Year’s resolutions are a big part of Bridget’s story. Starting the movie on January 1 lets her begin the diary with a fresh-start mindset, even if her plans don’t exactly go according to plan.

Last Word

These five movies offer five very different ways to spend a holiday evening. There’s the slow-burn friendship of When Harry Met Sally, the fate-and-timing romance of Serendipity, Bridget’s wonderfully chaotic attempt at a fresh start, the glossy ensemble madness of New Year’s Eve, and the much more emotional journey at the heart of About Time.

So don’t pick based only on which movie has the highest rating. Pick based on what you actually feel like watching. Sometimes you want something funny and familiar. Sometimes you want ridiculous holiday chaos. And sometimes you want a movie that quietly reminds you to appreciate the people sitting next to you.

That’s probably the best thing about New Year’s movies anyway. They can become part of the tradition, not just something you watched once.