I Saw 10 Ships: The Best Christmas RomComs

When you think of what children’s Christmas movies are really about – elaborate holiday fantasies about befriending Santa, visiting the North Pole, and getting the ultimate present – it’s a wonder that any kids like them at all. Real life never matches up.

You could say the same thing about holiday rom coms. I don’t know why I love watching attractive people fall head-over-heels in love (right in time for Christmas!) while sporting designer wardrobes. I could die alone in clothes from Target, but that won’t stop me from loving a good Christmas rom com. If you love rom coms too, make some time between now and 12/25 to see these three ten ‘ships come sailing in.

Traci’s Picks

Love Actually

What’s a Christmas movie list without Love Actually? Shit – is what it is. I remember going to see this with some friends in high school (at the theater Molly used to work at!) and immediately loving it about 10 minutes in. I was enamored with Christmas in London, hot Karl, Jamie and Aurelia’s unspoken love story, ‘Ifyou real-ly love Christtt-mas’ charming Prime Minister Hugh Grant, pre-fame Chiwetel Ejiofor & January Jones, everything about Emma Thompson, SAM – all of it. I bought the soundtrack and played it on repeat, even when it wasn’t Christmas. Needless to say, it’s not only one of my favorite Holiday RomComs, but all time movies in general. Besides Crash, Richard Curtis brought the intersecting storylines way of filmmaking into the the 2000s, and it’s been an influence on movies ever since.

The Best Man Holiday

Let’s be real. I only went to see this movie theater because of the impressive amount of HBMs (<- click for explanation). I hadn’t see the first one, but I figured I didn’t really need to know much about it, and they would recap me if necessary. And if you haven’t seen it either, the good news is that when you watch The Best Man Holiday, they’ll do just that. This group of longtime friends gets together for some quality time over Christmas, and while there are many laughs and near panty-dropping moments (like the one shown above), all I’m telling you is to watch with a box of tissues next to you. You will probably need them.

I’ll Be Home For Christmas

I wasn’t one of those girls into JTT. Just call me the 1%. I was too busy fangirling over Leo and BSB, I didn’t have time for a silly crush on a 90s It boy. However, I wasn’t exactly immune to his movies either. Like this one, a fun and festive adventure which has JTT speeding across the country in a Santa suit to get from California back home to New York in time for Christmas. Yes, that is Jessica Biel as his girlfriend. Yes, of course, the ride in a one-horse open sleigh together.

Bad Santa

Does this really constitute as a romantic comedy? Maybe not entirely, but these is some ‘romance’ in it, thanks to my girl Lauren Graham and her naughty relationship with Billy Bob Thornton’s Santa. He’s a disaster, but you know who really wins Christmas in this movie? THIS KID.

When Harry Met Sally…

When Harry Met Sally doesn’t entirely take place over the holidays, but a chunk of it does, and of course the end at New Year’s Eve, so I’m counting it. If you’ve read my previous post about this film, you’ll know that I was a late bloomer to this amazing movie, but I’m all in now. WHMS is a reminder that New York at Christmastime is a magical beautiful place – and then you snap back into reality watching Sally try to haul a Christmas tree by herself in the snow down the street. But all of it, the good and the bad, is a reminder why RomComs like this are the perfect thing to watch at the holidays. They make you laugh, make you cry, make you all tingly inside knowing that the season isn’t just about the trees and the snow and the presents – it’s about being around the people you love.

Molly’s Picks

The Holiday

The Holiday is one of my top two Christmas rom coms (it sort of shares first place with Love Actually). It has everything I could want in a Christmas movie: aspirational real estate (both the California mansion and the Cotswolds cottage), just-as-aspirational hair and wardrobe, precocious English tots, a kindly old man, and Jude Law right in the middle of what will someday be remembered as his golden era. Sure, it does fall into the romcom trope of everyone thinking the obviously pretty and charismatic Kate Winslet is some sort of sad sack, but – spoiler! it turns out she’s leading lady material after all. With Jack Black and Cameron Diaz rounding out the main cast, the Holiday is the perfect balance of rom and com.

Meet Me In St. Louis

As with regular-season rom coms, it’s important not to disregard the classics at Christmas. This musical (come on, you knew there would be a musical!) follows a year in the life of a turn-of-the-century family. However, the film ends at Christmas time, and is the origin of Have Yourself A Merry Little Christmas. To be honest, I never would have bothered with this movie if (1) I weren’t in the play in 8th grade, and (2) it didn’t star Judy Garland while she was still … doing well. But it’s worth watching if you like musicals, holiday cheer, and one of the most talented performers of a generation.

The Family Stone

I recommend this rom com with one reservation: I am recommending the whole thing except for the last, oh, five-ish minutes. If you’ve seen it, you know why. But the rest of it is great, sort of a Yuletide This Is Where I Leave You. And like TIWILY, it’s at least somewhat relatable if you have a large family of grown siblings, in-laws, nieces and nephews. The comedic parts of it hit a little harder than a lot of Christmas movies, which stick to the feel-good fluff. Plus, the cast is incredible: Christmas King Dermot Mulroney, as well as Diane Keaton, Craig T. Nelson, Luke Wilson, Sarah Jessica Parker, Claire Danes, Rachel McAdams,  Elizabeth Reaser and Paul Schneider (Mark Brendanawicz himself).

But I mean it about the last 5-10 minutes.

Elf

Elf, a rom com? I say that it is! It may be a children’s/ family movie, but I think it’s one of the funniest films out there. And I know I’m not the only one who thinks so, because just about every other adult I know can quote the whole thing. After a rocky start (the musical Law and Order: SVU episode setup that is Baby It’s Cold Outside), the gentle love story of Buddy and Jovie is a big part of what makes Elf so sweet. What can I say? Smiling’s my favorite.

While You Were Sleeping

If I had to explain to someone what 1995 was like, in the romcom world anyway, I’d show them While You Were Sleeping. This movie is just so delightfully normcore, before we had a word for it. Everyone’s hanging out in Chicago, wearing Gap sweaters and Land’s End khakis, telling lies about their romantic history and falling in love during comas and stuff. If you’re wondering why your mom still calls Sandra Bullock America’s Sweetheart, just watch While You Were Sleeping.

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Pop Culture Moments That Make Me Cry

Some pop culture moments are engineered to make you cry. Any time they show you an old man who is alone, or a beloved dog bravely facing his mortality, you know they’re trying to make you bawl.

Others aren’t supposed to be sad, but for some reason they grab onto your feelings and twist them until your eyes water. For instance: any time a child sings and it’s very beautiful.

Then there are those moments that were meant to be sad, but came out hilarious instead. I present for your approval:

This is the rare tearjerker scene that makes us weep – because we’re laughing so hard. So with Dawson Leery as our patron saint of pop culture crying, we’re listing those moments in entertainment that brought us to tears. Our scale stretches from one Crying Dawson (your eyes are lightly watering, but there’s no real tearstorm) to five Crying Dawsons (or as we like to call it, a Full Leery). And disclaimer: there will be spoilers ahead. Consider yourself warned.

One Crying Dawson1 crying dawson

  • The final, heartrending scenes of The Notebook. And I’m only putting it here because zero crying Dawsons wasn’t an option. I’m a monster, I know.
  • The end of Bridesmaids where Maya gives one last glance back at Kristen before she gets in the limo with her new husband. There’s an unspoken understanding between two best friends that just gets me.
  • Any time an actor/actress that is announcing Emmy/Oscar/Golden Globe nominations at the asscrack of dawn, only to announce their own name as one of the nominees.
  • Cyrus realizing he was the reason his hubs got killed on Scandal. You brought it on yourself dude.
  • When Little Michael Scott wants to grow up and have 100 kids so he can have 100 friends and no one can say no to being his friend.
  • The end of City Lights (taking it way back to the 1930s here!), when the blind girl sees the tramp for the first time.
  • When Mary is sort of mean to Martha in A Secret Garden but it’s because she doesn’t know how to play or love and her parents are dead and she lives in a creepy house in the middle of nowhere.
  • The “Love Is A Dream” sketch with Phil Hartman and Jan Hooks, serving the one-two punch of old people thinking about their youth, and people who died before their time.
  • When the now-elderly Peaches take a team picture and sing their song one last time in A League Of Their Own.
  • In The Great Gatsby, both the book and film adaptations, when Daisy delivers the “beautiful fool” line. Gut punch.

Two Crying Dawsons2 crying dawsons

  • When Papouli taught us about Greek dance, the love of family, and brief character arcs on Full House.
  • The look on Louis’ face when his daughter plays the violin duet with the neighbor on Louie.
  • The episode of The Simpsons where Homer gets the crayon lodged in his brain removed and suddenly becomes smart. At the end Lisa reads a letter he wrote her from before he got dumb again and it was the first time anyone in her family understood her.
  • Also, after Maggie is born and Homer goes back to work at the plant, he covers the mean plaque from Burns “Don’t Forget, You’re Here Forever” with her pictures so that it now reads “Do it for her.”
  • When Brian Williams reported on the NBC Nightly News that his daughter Allison Williams had been cast in the live version of Peter Pan. No matter what you think about the casting decision itself, you have no soul if you don’t get emotional watching him be so proud of his daughter.
  • Mr. Feeny dismissing class one final time.
  • Jen Lindley’s final conversation with Jack. And TBH, I might have cried more when Jack and Dougie declared their commitment to each other on the beach.
  • When Will believes his father isn’t going to leave him again on Fresh Prince of Bel-Air but Pops lets him down again, and Will breaks down in the arms of Uncle Phil asking why his dad doesn’t want him.
  • The voiceover at the end of The Time Travelers episode of How I Met Your Mother, when Future Ted says that he wants 45 extra days with The Mother… probably because at that point I had a pretty good idea of what that darn show was going to do to us.
  • Leslie saying goodbye to Ann on Parks and Rec. Uteruses before duderuses.
  • When Mel Gibson is getting ready to leave in The Patriot, and his mute daughter runs after him screaming “I’ll say anything!” Doubly so now that she’s passed away.

Three Crying Dawsons

3 crying dawsons

  • The final moments of that old dog in Homeward Bound.
  • The Muppets (2012), just in general. It made both of us cry and neither of us knows why.
  • Jessie singing When Somebody Loved Me in Toy Story 2.
  • The little girl singing Desperado in In America.
  • I was in a hotel a few months ago and came across a documentary on like the Travel Channel or something that was about the new Diagon Alley attraction in Harry Potter World at Universal Studios Orlando, and the planning, construction and attention to detail that went into it before they opened the doors. Before opening it to the public, a select group of young HP fans were let into the park as a sneak peak and the look of awe was astounding. I can’t imagine being a kid, being obsessed with the books & movies and finally being in Diagon Alley for real.
  •  In what is one of my favorite dances over all the seasons of So You Think You Can Dance, golden child Travis Wall choreographed an emotional contemporary (and Emmy nominated) piece to Coldplay’s Fix You, a dance based on his own experience of helping his mom through her bout with cancer. While Fix You is always a tearjerker, add on the brilliant dancing by Robert Roldan and Allison Holker and you have a piece of pure art that will leave you breathless.
  • Speaking of SYTYCD, season 11’s Ricky Ubeda was one of those winners who actually deserved the victory, thanks to his combination of talent and personality. But during Hollywood week, it was his solo that made me (and a lot of other viewers) single him out from the crowd, thanks to vulnerability and emotion he brought to the dance.
  • Lily telling Marshall his dad died on How I Met Your Mother.
  • The final scene in Friends when they all walk out of Monica & Chandler’s to go to Central Perk and there’s one final sweep of the empty apartment with swelling music in the background.

Four Crying Dawsons

4 Crying Dawsons

  • Carrie Underwood singing. Pretty much singing anything. Especially if it’s live. I’ve seen her in concert three times and every single time I was brought to tears. She sings with such passion and conviction. And if she’s singing any kind of religious song, you know she’s channeling the big JC, making her voice even more powerful for some reason.
  • The scene in both the book and movie version of The Fault in our Stars where Hazel is giving the ‘eulogy’ for Gus in the church.
  • The Normal Heart. All of it.
  • Friday Night Lights – pretty much the entire show. However, I’ll pinpoint one that stands out, which is when Coach throws Matt Saracen into the shower, but QB1 breaks down, insisting that his loved ones always abandon him. And to continue this Zach Gilford lovefest, the entire episode of The Son is heartwrenching, but I won’t ruin it for you if you haven’t seen it.
  • Call it the Jason Katims effect because Parenthood also makes me cry during every episode, no matter what. Again, it’s hard to pick just one, so the scene where Kristina tells the family that she has cancer – a scene so powerful with no words at all. This current season hasn’t been lucky for Zeek, and because of personal reasons, I’ve found his storyline extremely upsetting. Also Mae Whitman crying. Legit the best crier in the biz.
  • The series finale of Gilmore Girls in which Rory assures Lorelai that she’s “already given her everything she needs” before she goes on the road following Senator Barack Obama. In fact the final like 20 minutes of that show including Rory’s speech under the tent make me cry so hard that I’ve only watched the finale approx thrice, as opposed to like the 30 times for all the other episodes.
  • The finale of I ❤ Nick Carter where he and Lauren get married. Legit stayed up til 4am watching it and it was totally worth it. His family sucks but good thing they have the rest of BSB and other friends and family – that’s what got me.
  •  Jim Halpert learning he and Pam are having a baby after she injures herself at the company picnic. The whole office singing Seasons of Love to Michael on his last episode. The ‘Forever’ flash mob at Jim & Pam’s wedding and them getting married on the Maid of the Mist and Jim cutting off his tie. The entire series finale. I had a hard time saying goodbye to The Office.
  • The first 5-ish minutes of Up.
  • When Mary and Edith realize that they’re the only ones left after Sybil dies.
  • I was never big into Buffy, but that scene where Buffy tells Dawn that their mom has died, and you’re watching it through the window of her classroom? Nope.
  • DOBBY. RIP.

Five Crying Dawsons

5 crying dawsons

  • The Quarterback episode of Glee where Finn (Cory Monteith) dies. I literally went through almost an entire box of tissues during that and I’m not even a huge Glee fan. The pain on everyone’s face was real, and watching Lea Michele sing – forget it.
  • The end of The Best Man Holiday – what in the fuck was that all about?! I paid $15 to see Taye Diggs and his fellow HBM co-stars possibly take their clothes off and it turned out that I needed extra sleeves because my tears and snot were all over the shirt I went in with.
  • Right before Leslie and Ben get married, when she’s talking with Ron in the hallway. I’m a wedding crier anyway, but jeez.
  • In Little Women, when Jo is going through the trunk in the attic after Beth has died (note: Beth’s death gets knocked down to 4 Crying Dawsons because of the weird brogue Claire Danes starts speaking in).
  • Everything that happens after Sara Crewe goes to live in the attic in A Little Princess. This is the second Frances Hodgson Burnett appearance on this list so I hope wherever she is, she’s proud of her vast legacy of children’s tears.
  • The funeral scene in Philadelphia, when they show the home movies of Beckett as a kid with his mom.
  • Good Will Hunting: 4 words – “It’s not your fault.”
  • My Girl: 6 words – “He can’t see without his glasses!”
  • Dead Poets Society: 4 words – “O Captain! My Captain!”