50 Favorite Romances: The Wonderfully Awkward/Realistic Ones

Look at how I am finally finishing my list! Guys, since in real life I am pretty awkward (SHOCK), I have a special place in my heart for on-screen romances that can capture the adorable awkwardness of an early romantic relationship* and the magic that can ensue in the long run. I find it heart-warming if sometimes difficult to watch because I am also like, "Word." Here's those guys.

Also see: 1-10: The Sweet Ones, 11-20: The Sexy Ones, 21-32: The Slow-Burning Ones, and 33-38: The Devastating Ones.

39. Bridesmaids (2011)

You can't be throwing away the ugly carrot like that. It's lucky!

Um, so fucking cute? Mostly this movie is about Kristin Wiig's character being a wreck because Maya Rudolph is getting married/got a new best friend, but the romantic B plot with Chris O'Dowd as an adorable (Irish) Milwaukee cop she keeps running into is wonderful. Their interactions are cute and awkward and messy, just like real people's! Also, IMDB just told me he is on The IT Crowd, so I should probably stop letting it fester in my instant queue and get on watching it.

40. Harold and Maude (1971)

Let's go steal some cars and whatnot.

I think a sixty or so year age difference works perfectly in this movie. Harold is obsessed with death. Harold is awkward and wears amazing seventies suits and goes to funerals for fun. And Maude, well, Maude is wonderful. And I'm glad they like each other. Fuck you, other people. Meaningful connections can be hard to come by.

41. Head-On (2004)

He didn't really tidy up before he brought her home.

They meet in a mental institution. She wants to get away from her strict family, so she marries the first Turkish guy who will agree to so she can move out and drink and party and have lots of meaningless sex. Sham marriages never stay shams according to movies and TV, though! Their eventual emotional entanglement is both awkward and sexy in its development and feels very natural. A tragic plot twist about 2/3 of the way through made me seriously consider putting this on the "devastating" list. You have been warned.

42. How I Met Your Mother (2005- ) - Lily and Marshall

How can you not love a couple that does stuff like this?

Lily and Marshall are best friends. They are drinking buddies. They love each other so much. I love them. I want to be their friends.

43. Humpday (2009)

Masculinity at its finest dumbest.

Bro 1's old friend Bro 2 comes to town and through a series of events/conversations that are not important/I don't remember, Bro 2 effectively challenges Bro 1's masculinity because he's all married and whipped and shit. Basically Bro 2 (beard) convinces Bro 1 (Pete from The League**) to do a gay porn movie with him. OBVIOUSLY. Bro 1 convinces his wife this is something he has to try to do, and a lot of the movie is the two bros in a hotel room, trying to convince themselves to get it on with each other. I kept yelling at them to drink more, but their friendship and their internalized homophobia are examined in their attempts during this "Mumblecore" movie.

44. Medicine for Melancholy (2008)

Yep. Hipster Wyatt Cenac in all his bearded glory.

Micah and Jo hook up drunkenly at a party. In the morning, they don't remember each other's names. Micah wants to get to know Jo/make some more happen. Jo is technically in a relationship (with a white dude), and finds Micah somewhat exasperating. They basically spend a weekend together exploring what might be, having fun between discussing what it means to be black on the "scene" and interracial relationships and gentrification and history and race in general. It's awkward and very real feeling. You want things to work out, but understand why it probably can't. There's a reason "melancholy" is in the title. Wyatt Cenac's character is a fish tank designer or something. OBVIOUSLY. Also, Tracey Heggins is STUNNING and kept reminding me of my friend Anne. (Not-so-subtle peer pressure to write more, friend!)

45. Moscow, Belgium (2008)

One of the sexiest propositions I've ever seen onscreen. Awkward and honest. Love.

In this wonderful, wonderful Flemish film from 2008, Matty and Johnny awkwardly fall in love. Matty, a lady in her '40s who is actually still super-hot but wears terrible frumpy clothes and works at the post office, is separated from her philandering husband of many years, taking care of their three precocious children in a kind of sad apartment complex. Through a typically unlikely romcom scenario, she meets Johnny, a truck driver who is supposed to be 29, but clearly the actor is much older than that, but whatever SUSPENSION OF DISBELIEF PEOPLE, IT'S THE MOVIES. Johnny pursues Matty, she insists she just wants her husband to come home. Her husband only wants to come home when he thinks she's moving on. The oldest daughter has started dating, Johnny has a kind of a horrifying past (which apparently I can look past because he's so cute and sweet otherwise?), and shenanigans ensue. LOVE LOVE LOVE, RECOMMEND RECOMMEND RECOMMEND. I own this movie. So good.

46. Paper Heart (2009)

Team hoodies!

Yes, Michael Cera always plays awkward, sweet young guys. But I think maybe he is that guy? And in this movie he plays himself: an awkward, sweet young guy and a rising star. Charlene Yi (who I adore and saw most recently on TV's House playing an awkward doctor) plays herself in this mockumentary, and despite all the press that claimed they were real-life lovers, supposedly they were never actually a couple or whatever. Whatever. Anyway, up-and-coming Charlene lives in L.A. and doesn't believe in love until she meets adorable Canadian actor Mike. An awkward long-distance romance full of false starts (like real relationships, duh) ensues, kind of throwing a wrench in Charlene's "love is fake" documentary that is supposedly driving the movie. Got it?

47. Parks and Recreation (2009- ) - DOUBLE COUPLE CUTENESS TROUBLE

If you know me, then you know I love me some Parks & Rec HARD. I own a Lil' Sebastian t-shirt and plush toy, people. Don't fuck with me. And so it's kind of cheating throwing two romances in under one title, but I can't choose between them, so DON'T MAKE ME. First, of course: Leslie and Ben.

I support your professional ambitions so hard. Let's go do some sexy politics nerd cosplay, mmkay?

Leslie Knope is amazing an wonderful and feminist and good at everything and Ben is played by the Sexy Gay Jesus' gift to people with eyes AKA Adam Scott and they are so nerdy and so sweet and even after their love was no longer forbidden, I was totes into it. Also, remember when Ben punched that dick in the bowling alley and Leslie was so into it? LOVE IT.

Burt Macklin, FBI and Janet Snakehole FOREVER!

There are couples out there like April and Andy, where both person on his or her own is kind of terrible at life and relationships, but together they are not necessarily better at those things, but they are so perfect for one another that it no longer matters. When April and Andy got together and very shortly thereafter got suprise-married, I was touched. Yes, I felt feelings in my cold, blackened little heart. April is the epitome of sarcasm and cynicism (which is why my husband secretly wants to leave me for her, but it is okay as long as I get Adam Scott in the tradeoff), Andy is the epitome of pure, unadulterated enthusiasm. And by unadulterated, I really mean so not adult in any way. But I love them together. I love how April sometimes accidentally smiles when Andy's around and how Andy thinks April is so awesomesauce, that it doesn't even matter that she rarely smiles, she's always up for his wacky plans. Those two + Champion = America's Greatest Family, basically. Also, Ben lives with them, which doesn't hurt.

48. The Trotsky (2009)

This really shouldn't work, but it might?

I don't even know if the love story in this movie really quite works, but since I find Leon (Jay Baruchel) pretty irresistible in this movie, I can understand why sexy older lawyer lady Alexandra falls for him. The movie is mostly about how Leon believes he is the reincarnation of Trotsky. OBVIOUSLY. He organizes a strike in his dad's factory, who punishes him by sending him to public school, where of course he finds more reasons for the proletariat (students) to rise up. He's brash and deluded and way too smart for his own good. Cute and Canadian and wonderful, I say.

49. While You Were Sleeping (1995)

I'm fake-engaged to your brother in a coma, but who cares because of cute cuteness?

The first couple times I watched this movie, I found the parts when Lucy gets drawn into the Callahan family kind of painful to watch because of unnecessary misunderstandings and whatnot. But after dozens of viewings over the years, what I still appreciate is the very real (and sweet) chemistry between Sandra Bullock and Bill Pullman (never this cute again) and the very witty writing. Cast aside your prejudice against the terrible romcom plot conventions and see how AMAZING the family's dialogue is, how fucking clever and quotable and fantastic. This movie offers no great surprises or subversive messages, but it makes me feel good. I try to watch it every Christmas season at least. And if you and your sixth grade best friend haven't rewound the VHS tape over and over again to see the paper boy biff it on repeat, then you have not lived my friend. There's also a reason this made my sister's list, too. It's a classic, people.

50. William and Mary (2003-2005)

People on TV have never seemed so normal.

I became curious about this British TV show soon after I got obsessed with Doc Martin (an earlier entry on this list), because I couldn't understand how such a funny looking guy (Martin Clunes) could be so irresistibly attractive. I'll admit I haven't seen series 3 because it's (still) not on Netflix, but I'll have to track it down now that I've realized it exists. Mary is a midwife and William is a reluctant undertaker (family business). They meet and somehow manage to actually start dating. They each have two kids and are trying to manage single parenting, jobs, life, and each other. There's something very natural and very real about the way they interact. Neither of them is American TV gorgeous, and the way that real-life stresses get in the way of their connection at times is so much more realistic than horrifying family secrets or secret blindness or one person being a robot or something. Highly recommended. Now I've got to figure out which web TV service will let me watch the rest of it without waiting forever for buffering or having to download sketchy software.

THE END. 

*Nothing awkward ever happens later on. Or rather, you get used to each other's awkwardness.

**I know this looks like such a bro show, and it is about a bunch of bros (and one lady), but it is SO funny and definitely worth watching past the short first season. Mostly it's about people being terrible to each other (though not as terrible as the terrible, terrible characters on It's Always Sunny in Philadelphia, which I also love). The football nonsense is not really important to follow.