Countdown to Christmas: Holiday Date Night Movies

Friday nights are the quintessential date nights. David and I have always said that we aren’t “date people.” We’re movie people. Getting dressed up and sitting across from each other at a fancy restaurant? Not really our thing. We have to do that for work all the time, so it never really feels all that special. Our idea of an awesome date is heading to the movie theatre or, more often than not, staying in with a movie and a pizza. People assume that we have to stay in because we have kids, but that just isn’t the case. We did the same thing when we were in high school and in college. Anyway, if you’re into our kind of date night (or if you are forced into it because you have no other option) here are some of our favorite holiday movies to watch together:

Love Actually: One of my all-time favorite movies. I just wished I hadn’t gone on and on about and then agreed to watch it with my grandfather, totally forgetting about the f-bombs and the porn stand-ins. Thankfully, I’m fairly confident that he slept through most of it. I love everything about this movie. This is a great ensemble about finding love in the time leading up to Christmas. It celebrates love in all shapes and forms. Every single story line warms my heart. Well, all except one (and this is a spoiler, so if you haven’t seen the movie, stop reading). The one where Alan Rickman (you know, the bad guy from Die Hard and Robin Hood: Prince of Thieves) buys a fancy necklace for someone that isn’t his wife and then she finds out about it and is heartbroken was not so heartwarming. This film boasts one of the best Christmas songs ever (I feel it in my fingers… I feel it in my toes…).

While You Were Sleeping: Speed made people notice Sandra Bullock. This one made her a star. I seriously wore out my VHS copy of this one back in the day and I cannot even tell you how often I watch this DVD.  On a side note, my son saw a VHS at my parents’ house today and had no idea what it was. That made me feel old. But I digress. Anyway, my oldest son is a huge Sandra Bullock fan, so he never objects when I want to watch this or The Proposal. It is all about Lucy, a Chicago Transit Authority Employee who rescues her crush from being crushed by a train on Christmas day. When she is at the hospital she is mistaken for his fiancé. Before she can clear up the mistake right away, they invite her to spend Christmas with them. Because she is lonely she accepts and quickly finds herself falling in love with his entire family and then she can’t find it in her heart to tell them the truth.

Fools Rush In: The film opens with Matthew Perry’s character walking into his company’s Christmas party carrying a giant stuffed marlin and things only get better from there. This was probably the first time I noticed Selma Hayek (and David really noticed her…as did every other male in the family). The movie was panned by critics but it is an all-time favorite in our house. It is all about a one night stand that turns into something more when she shows up unannounced to say that she’s having his baby. They are from such different worlds that they aren’t quite sure what to make of each other. His attempt at bonding with his family ends in disaster and when she meets his parents for the first time, they think she is the housekeeper, which also doesn’t go over so well. This is an example of opposites attracting at their finest.

The Family Man: Nicholas Cage is awesome in this movie. Seriously awesome. It is a Capra-esque film about a single man who thinks he has it all, getting a taste of what his life might have been like had he made different choices. It is like the reverse of It’s a Wonderful Life. I’ll never understand why Nicholas Cage doesn’t make more films like this because he is so good in romantic comedies (Bangkok Dangerous? Not so much). Téa Leoni shines as Kate, the one that got away and Don Cheadle is fabulous as the angel. If you really pay attention you might notice Kate Walsh, Amber Valetta and Robert Downey Sr., who all have  in a small parts. I also love pre-Entourage Jeremy Piven as his best friend (remember back in the day when he always played the best friend, especially to John Cusack… Speaking of Jeremy Piven and John Cusack…)

Serendipity: This movie, starring John Cusack and Kate Beckinsale opens and closes with scenes of Christmas time in New York . It is about a couple who meet by chance one night while Christmas shopping and really hit it off. He wants to get her number but she believes if they’re meant to meet again, fate will bring them together. Years later, they are both about to marry other people (played by Bridget Moynahan and John Corbett), but at the last minute, each decides to search for the other with the help of their best friends, played by Jeremy Piven and Molly Shannon. The story is a bit predictable, but very enjoyable and there are some laugh out loud moments courtesy of Eugene Levey as a bumbling Bloomingdales salesman who both helps and hinders their reunion. David and I find ourselves quoting this movie all the time.

The Holiday: I think I like this movie so much because I can identify with parts of each of the main female leads (Cameron Diaz and Kate Winslet). This movie is about two women, one in L.A. and one in the English countryside, who decided to swap houses for Christmas and who end up finding love along the way. I fall in love with Jack Black’s character every time I see this movie. Then I see how sweet Jude Law’s character is with the little girls (who are absolute dolls, by the way) and I fall in love with him too. And then I see Eli Wallach and he is so stinking cute that I fall in love with him too (strangely enough, I don’t feel the same way when I watch the Good the Bad and the Ugly with my dad). It gets bonus points because John Krasinski has a small role as one of Cameron Diaz’s assistants. And who doesn’t love John Krasinski? 

Mystery, Alaska: This movie is about a small Alaska town named Mystery (as if you couldn’t garner that from the title) where hockey holds court. Although Christmas is not a central theme, the film takes place around Christmas. The entire town lives and breathes by “The Saturday Game” where the town’s finest compete each week in a game of pond hockey. After an article featuring the town and its hockey tradition runs in Sports Illustrated, the team is challenged to play against the New York Rangers. With their reputation on the line, the entire town has to come together to make it happen. Every time I watch this I want to move to a small town in Alaska. I love the gorgeous setting and the quirky characters. Then David reminds me that I would have to live somewhere that it snows and that I’m basically a hermit and I am immediately brought back to reality. I always get points with the guys when I pick this movie because they think of it as a hockey movie. I think of it as that hilarious movie where Russell Crow looks super-hot.

When Harry Met Sally: I’m not going to lie. When I found out David was Hungarian, It was all I could do not to say, “Waiter… there is too much pepper in my paprikash.” (I no longer hold back and insist on saying this every time we have chicken paprikash, even if I’m the one who made it). This film is about plutonic friends who can’t seem to be in successful relationships with the opposite sex. Could it be because they are destined to be together? This goes on our Christmas list because it has Christmas scenes. It also stars Princess Leia, so you know it’s a good movie. And did I mention that it was written by Nora Ephron. For those of you who don’t know, I want to be Nora Ephron when I grow up. She is hillarious. And it is directed by Rob Reiner, who is one of my favorite directors. I could go on. If you haven’t seen this one, you must.

Sleepless in Seattle: This one is about a woman in New York (Meg Ryan) who hears a widower’s (Tom Hanks) sad story on a radio call-in show on Christmas Eve and cannot shake the feeling that they are meant to be together. She writes him a letter (as do thousands of other women) and his young son becomes convinced that she is the one and sets out to bring them together. He is not so convinced and continues allowing friends to set him up on dates with other women, causing him and his son to butt heads. It has a great supporting cast (Rosie O’Donnell, Bill Pullman, Rita Wilson), a cute (if predictable) story and an excellent soundtrack. And while tracking down a man, flying across the country and staring at him while he plays with his son might be considered stalking in the real world, in the movies it is romantic.

You’ve Got Mail: Another Meg Ryan and Tom Hanks hit, this one is an update of classic Hollywood film, The Shop Around the Corner. In this film Hanks and Ryan play anonymous email pen pals who are also archenemies in the business world. She runs a cute little children’s bookstore and he runs a chain of book superstores that are threatening to put her out of business. They hate each other by day and unknowingly confide in each other through emails at night. What could possibly go wrong? This one makes our Christmas movie list because a significant portion of the film takes place around Christmas. Her quirky employees and his insane modern family dynamic (his aunt and his brother are both very young children) make an alreadya great movie, shine even brighter.