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Vulture Watches You’ve Got Mail With Mindy Kaling

Mindy Kaling — best known for her work on NBC's The Office (as writer, producer, director, and actor) — has a humble dream: to write the definitive romantic comedy for her generation. Her favorite is You’ve Got Mail, Nora Ephron's 1998 classic about Tom Hanks and Meg Ryan finding love on the Internet — or AOL, as the Internet was called in 1998. Kaling, who is in the midst of working on her own romantic comedy, The Low Self-Esteem of Lizzie Gillespie, agreed to watch the movie with us, which led to discussions about everything from the genius of Woody Allen to Nancy Meyers movies to the perfect rom-com stars (her Office co-star, Ed Helms, will be very happy).

What makes You've Got Mail your favorite?
Some friends of mine think it’s the worst movie ever. They hate it. I don’t get it. People love Sleepless in Seattle — they put it on the same level as When Harry Met Sally. But I love You You’ve Got Mail. I think people forget about the great ensemble cast: Greg Kinnear and Parker Posey are in fairly tiny roles and are such heavyweights. Dave Chappelle has, like, six lines. But, for me, the secret weapon is Meg Ryan’s fashion. She plays the owner of a bookstore, but dresses like a female comedy writer. Nothing is very fitted, everything is four sizes too big. It’s Diane Keaton slouchy clothing on a really pretty girl who went to Sarah Lawrence — MFA fashion.

Nora Ephron fashion is more like it. The music is great, too.
Yeah, that wonderful Cranberries song, “Dreams,” which everybody was playing then. And Joni Mitchell’s “River,” for the scene where Ryan is twirling around in her mother’s clothes. And that great Randy Newman song, “Lonely at the Top.” Lots of the music makes me cry, which suits the film. Ryan’s character has so much to be sad about. Her bookstore — the great love of her life — goes out of business. Her mother, who is her best friend, is dead. She’s with a man she doesn’t love [Kinnear]. And yet she’s so upbeat. We don’t have to watch the whole thing, by the way. I used to watch it in fifteen-minute intervals — like when I would do sit-ups after a run. Watching any fifteen minutes of this will make me feel cheered up and then I go do something else.

What about the romantic comedy you’re writing? What’s it about?
It’s in preproduction. I wrote it with [Office writer] Brent Forrester. We sold it to Mandate, which was the studio that did Juno. It's about a funny girl who's had low self-esteem since she was a teenager, and so she always gravitates toward ugly losers because she figures she'd never be able to date anyone attractive or cool. [At this point You’ve Got Mail begins]. This is such a goofy beginning! It’s so dated! This was when it was still miraculous — at least to Nora Ephron — that e-mail would get sent. They’re making it like it’s a supernatural thing. Look, Ryan’s computer’s plugged into the wall! So hilarious.

When did you first see this?
When I was 18 and an intern at Conan. Oh, I love this Sims graphic! Anyway, I was very intimidated by New York and I didn’t know it very well, and this movie really helped me, it made me fall in love with the city — it’s such a love letter to New York. I went to all the places in the film. And I decided that I love the Upper West Side. I remember watching it during Christmas and thinking, I wonder if I’ll ever have a really cute boyfriend like Tom Hanks, and sing carols around a piano? I love this line, where they say Parker Posey’s character makes coffee nervous. There are great jokes in here. Do you notice how they made everyone look so middle class and regular? And yet Ryan’s apartment is huge …

They always do that in big romantic comedies. Everyone has amazing apartments.
I love that. I’m glad this doesn’t have the veracity of some mumblecore film.

People criticize Nancy Meyers's movies for the fabulous interiors.
If you’re going to be the type of person who goes to see a Nancy Meyers movie, then don’t take offense to seeing a really nice kitchen! That person doesn’t add up to me.

Why do you think good movies about the Internet are so rare? Did you see like Must Love Dogs with John Cusack? It was terrible.
No, I missed that. But, yeah, we find this with The Office as well. So many funny stories and interesting things come from posts on Facebook or Twitter — things you’ll be talking about all day. But it’s so hard to make it dramatic. When romantic comedies include dialogue like, “He was a 5 and she wanted to date a 9” — no one talks like that in real life. I hate that.

Are you trying to remedy that with your movie?
When I write I don’t really acknowledge what the style is, I just write what I’m interested in and the way I talk and the way my friends talk. But, yeah, I love realism in writing, and especially in dialogue. It’s true that You’ve Got Mail isn’t all that realistic — all the peeking around corners and girls blowing bangs out of their faces and stuff. Lots of the direction was probably, "Be cuter! Try to be more adorable!" But I adore it anyway. Judd Apatow was the first person to write dialogue of guys talking the way guys really talk — like when they talk about the film Munich in Knocked Up. People were like, you can do this? You can reference other things? That was just cool. But I’ve never seen it with female characters, and that, essentially, is what my movie’s about — female friendships, plus a love story.

That’s why women liked Sex and the City so much, even though reality was obviously heightened. There are so few realistic representations of women together onscreen.
You seem ungrateful when you complain about that or hate on it, but it’s hard because you rarely see anything of women with other women that’s really, truly funny.

Who are some of the young actresses who can pull off funny?
I loved Reese Witherspoon in Election and Legally Blonde. She’s funny and fully a character actress, even though she’s gorgeous.

What was her last movie?
Four Christmases?

That was underrated.
There are incredibly funny group scenes in that, and Jon Favreau was hilarious. [Kaling notices an outfit in You've Got Mail.] This movie is very unisexual, very restrained. You see so many romantic comedies now that are R-rated. Maybe it’s Meg Ryan. Do you ever see anything above her elbows? Has she ever worn a tank top? Even if she did, she’d still be very pristine.

Do you have a sex scene in your movie?
It’s a scene between the lead, who hates her body, and this gorgeous guy who likes her, and I’m trying to realistically show — without being, like, "Keep the lights off" — what it is like if you are uncomfortable with you body. I ask a lot of guys, "What are you thinking when you’re about to have sex with a girl?" And the overwhelming feeling is that they just want to have sex. At the point where clothes are being taken off, they’re just excited to see a woman naked. They’re not thinking about physical flaws. I thought that was cute and a little bit reassuring.

It’s funny the disconnect about what you think the guy is thinking.
I’m constantly surprised. You hear these things in movies, guys saying, “I like you better without makeup.” And you’re, like, Nobody likes that! I don’t have a very romantic-comedy life, but when I recently climbed into bed after washing my face, my boyfriend said, “You’re so pretty without makeup on. Why do you wear it?” Now, I like wearing makeup, and I always will, but I thought, Thank you, God, for this sweet moment.

Are you a fan of Bridget Jones's Diary?
Another of my favorite movies! And it has a connection to You’ve Got Mail, since Bridget Jones is a version of Pride and Prejudice — another of my favorite movies — and Pride and Prejudice is Ryan’s favorite book in You've Got Mail. It's great when your favorite movies are sort of talking to each other. I’m working on a series for NBC right now that was inspired by Bridget Jones. I’m not skinny at all. I’m five-foot-four and wear size eight on a good day. But I’ve never not been able to date people I like, even though I constantly wish I was skinnier. And most women have my body type, and I’ve led kind of an interesting life, so why shouldn’t I be on TV? The main character is a sillier, slightly more confident version of me, and I’m writing the part for me to play. She’s a publicist for a PR firm. Anytime I play a role in anything, it will be a version of myself.

Like Woody Allen.
Right. People assume my comedy idol would be Tina Fey, and she is a great hero of mine. She’s done so much of what I want to do and she’s so good at it. But Woody is the ultimate. He believed in himself enough to do what he did. And I have that same feeling — that there’s nobody who looks like me in movies, that nobody should actually cast me as a romantic lead, but I want to do it anyway and feel oddly confident that I can. [She notices Greg Kinnear in You’ve Got Mail.] This I love. I know this guy — Kinnear’s character, with his typewriter, is so literary and snobbish. But the fact that he lives on the Upper West Side is crazy to me. He’s so Brooklyn.

This was a different time. Those people didn’t live in Brooklyn then.
Yes, true. You know, yet another reason I love this movie is because it’s populist, which I strive to be. I feel like the Kinnear character represents the pretentious guy, who I have definitely dated, and Tom Hanks is the unpretentious guy, even though his character is very rich. Hanks is one of the sexiest guys ever.

At first those pretentious guys are attractive, and then you get to know them and it’s boring.
I guess having no money is only sexy if you’re kind of awesome. If you have no awesome and you’re a dick snob, then it’s just another bad situation. I’d like to write about that — how when you’re 30 and a woman, you’re an adult. When you’re 30 and a man, you can still be a boy. Oh, this is one of my favorite lines in the film: “That’s why it costs so much, that’s why it’s worth so much.” I also loved that line in When Harry Met Sally — “When you meet the person that you want to spend the rest of your life with, you want the rest of your life to start as soon as possible.”

How did you feel about The Devil Wears Prada? Did it bug you that the main character walked away from a good job at the end, to go back to her boyfriend — like that was the only way she could be happy?
I felt like they tried to buy it back by saying what she really wanted was to write political pieces at her temp job. That was a hokey part of the story. At least she wasn’t a klutz. So many comedies and TV shows make pretty, skinny women klutzes — they have no discernible flaws, so let’s make them a klutz!

Like Liz Lemon.
Debra Messing was always doing that on Will & Grace.

It’s such an old trope.
The other one is actresses who clearly starve themselves playing characters who get picked on by the guy for eating too much.

In Valentine’s Day, the Jessica Biel character does that. When she gets nervous she shoves food into her mouth. Of course, it’s okay for Biel to do that because she’s in the best shape of any woman alive, so shoving food in her mouth isn’t offensive.
It would be so funny if an actual fat woman shoved food in her mouth. People would be horrified! They’d want to kill her! Is that an Onion headline? Actual Fat Woman Shoves Food in her Mouth in Romantic Comedy!

Do you like Nancy Meyers movies?
I feel a responsibility to support her in her successful endeavor to be the most famous and watched female director.

That sounded like a very diplomatic answer.
I’m incredibly not diplomatic. But I do appreciate that Meyers made a movie with the fantasy life of a 60-year-old woman. That’s pretty cool. I really did like Something’s Got to Give. You know what’s sweet about Hanks and Ryan here? Their innocence. They act like people who have had sex three or four times and they are fully in their 40s! So many romantic comedies today should be called sex comedies. There’s no romance. Characters say things like, “This is how you get a guy: You have to eat a hot dog like it’s a penis.” What? Who talks like that? You've Got Mail is the most soul-mate-y of soul-mate movies.

Do you believe in soul mates?
No. I’m really practical, which I think people don’t think about me because I love romantic comedies so much. But you need it in movies, otherwise there’s nothing to watch. I don’t need to see the movie about the people who just settle for each other because they were the right age and the closest approximation of their ideal. That might be what life is all about, but I don’t want to see it. I want to see the rich populist and the artsy tomboy fall in love despite their differences and just make each other laugh. [A Meg Ryan voice-over catches Kaling's attention.] I usually hate voice-overs — it’s such a gross trick — but it works so well for Ryan’s character because it feels organic. This movie has so many nice reveals. New comedies don’t have that — secrets where one person knows and the other doesn’t. Oh man, here’s where you find out these two characters are both cheating.

And the movie maintains that it’s not major.
It’s that great thing — if you’re really supposed to be with someone, cheating doesn’t matter. That’s the thing about Woody Allen and Soon Yi [with whom Woody cheated on Mia Farrow]. People forgave him because they’re still together and they’re in love and they had kids and made it work. They were supposed to be together. And if that’s not against all odds, I don’t know what is. It’s actually a bit romantic.

Who are the Tom Hankses of today?
I have high hopes for Chris Pine. I loved Star Trek. He could be Ed Helms — he could be Helms-y. I find Ed hot — straight-up hot. It’s weird to say about a friend, but I was looking at him the other day, when he wasn’t wearing his glasses, and he has this great body and plays guitar — he’s coming into his looks. I feel like when I see an episode of Bosom Bodies and Hanks starring as this ridiculous character on a campy show — maybe that will be what Ed was on The Office.

There don't seem to be a lot of hunky leading men right now.
And there are so many interesting actresses: Carey Mulligan, Alison Pill, Emily Blunt. They are all funny and capable of nuanced stuff. With guys — I miss the big guys. So many actors today are tiny and skinny. I don’t get it. I’d rather have 230 pounds than 130 pounds. Is that weird? A ruddy, strapping hipster guy would be very attractive. Does that exist? Maybe I love You’ve Got Mail because it’s kind of conservative. I’m pretty conservative — my parents are both Republicans. In my office, I’m the most conservative person in an extremely liberal environment — a bunch of bleeding-heart liberals form Harvard and me, the contrarian. I like to be the voice of reason.

Did you hear that the Barnes & Noble in this film, the one on 66th Street, is closing?
I did! I had this fantasy about a scene in a romantic comedy where I would go there, realize it was closed, and run into a guy who had the same idea. And then we’d walk to the next Barnes & Noble together and fall in love! It was an incredibly specific and also plagiaristic You’ve Got Mail meeting-a-guy fantasy. But that’s how I spend 90 percent of my time — having romantic-comedy fantasies in which I’m wearing little pencil skirts and hurrying down to the subway.

Photo: Michael Buckner/Getty Images