The witty and likeable, lightweight, old-fashioned romantic comedy, When Harry Met Sally... (1989) was intended to answer the sexual politics question:

"Can two friends sleep together and still love each other in the morning?"

The engaging, episodic film keenly observes romance, relationships between males and females, friendship and sex. Two long-time acquaintances Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) grapple with this question over a 12-year period (beginning in the spring of 1977), as their relationship grows and matures. Their love is not "at first sight" but takes years to develop.

[Note: Their contrasting names reflect their polar-opposite attitudes toward life: the dark, angst-driven, eternally pessimistic but warm nature of the male, with the bright-eyed, perky, fresh-faced, effervescent and happier character of the female. In fact, Harry says early on, "When I buy a new book, I always read the last page first. That way, in case I die before I finish, I know how it ends. That, my friend, is a dark side." He is basically sexist and irascible, while she fights back in a persnickety, eccentric, feminist way.]

The film's sole Academy Award nomination was for Nora Ephron's Best Original Screenplay - written directly for the screen - it lost to Tom Schulman's script for director Peter Weir's Dead Poets Society. [Note: Ephron would go on to write and direct other romantic comedies, including Sleepless in Seattle (1993) (with Rob Reiner in an acting role) and You've Got Mail (1998) (both with Meg Ryan and Tom Hanks). The respective films were updates of the two classics: Leo McCarey's An Affair to Remember (1957) and Ernst Lubitsch's The Shop Around the Corner (1940).]

The film also features the music of Sinatra reincarnation Harry Connick, Jr. This was one of cinematographer Barry Sonnenfeld's last efforts in that role - he went on to direct The Addams Family (1991) (his directorial debut film) and Addams Family Values (1993), Get Shorty (1995), and Men in Black (1997), among others. The solid lead roles and the supporting performances of the leads' best friends were neglected for Oscar consideration: Carrie Fisher as Marie and Bruno Kirby as Jess.

Director Rob Reiner directed this smart, modern-day 'screwball comedy' (his fifth film) of the semi-autobiographical tale - it was compiled from the shared recollections of actual romances. Reiner's first four films include the satire of rock documentaries titled This is Spinal Tap! (1984), the teen romantic comedy The Sure Thing (1985), the youthful drama Stand By Me (1986), and the delightful fantasy The Princess Bride (1987). In 2004, the film was adapted for the stage by Marcy Kahan, and opened in London with leads Luke Perry and Alyson Hannigan.

The summer of 1989's 'sleeper' film has a number of startling resemblances to Woody Allen's witty, urban romance Annie Hall (1977): the title credits (with a black background and white text) along with the film's title song "It Had to Be You" (sung by Diane Keaton in Allen's film) being played on a piano, direct camera interviews-testimonials, split-screen techniques, the Manhattan backdrop (including the fall foliage), evocative George Gershwin tunes, obsessive talk about sex and death, the romance between a Jew and non-Jewish woman (shiksa), and Harry and Sally's first meeting in 1977 - is the year the similar film was released. The film's ending parallels Allen's Manhattan (1979). However, the two films also differed: When Harry Met Sally... illustrated how friends can ultimately realize that they're better as lovers, while Annie Hall (1977) showed how lovers may end up better as friends.

The title of the film was spoofed in Dumb and Dumberer: When Harry Met Lloyd (2003).

The film opens with an older couple sitting on a love seat. [This is the first of many such pseudo documentary-style scenes of recollections of older couples describing how they first met. They are actors in the roles.] Speaking about his successful marriage, the balding husband talks directly into the camera with his white haired wife next to him:

I was sitting with my friend Arthur Kornblum, in a restaurant, it was a Horn and Hardart Cafeteria, and this beautiful girl walked in - [he gestures toward his wife] - and I turned to Arthur and I said, "Arthur, you see that girl? I'm going to marry her." And two weeks later we were married. And it's over fifty years later and we're still married.

UNIVERSITY OF CHICAGO - 1977

The film fades into a scene on a university campus. In close-up, a couple, twenty-six year old Harry Burns (Billy Crystal) and his twenty-year old girlfriend Amanda Reese (Michelle Nicastro) are confiding their love to each other and kissing madly. They are oblivious when a yellow station wagon drives up behind them with twenty-one year old Sally Albright (Meg Ryan), Amanda's pal. After their college graduation, Sally is driving Harry, her best friend's boyfriend, to New York from their school in Chicago - it will be an 18 hour trip.

Sally is blonde, smiley, clean-living, structured and very organized in an uptight way and she has already planned the entire trip:

I have it all figured out. It's an eighteen-hour trip, which breaks down into six shifts of three hours each. Or alternatively, we could break it down by mileage. There's a, there's a map on the visor that I've marked to show the locations where we can change shifts.

On the other hand, Harry is more of a slob, as he demonstrates by eating grapes and forgetting to roll down the window when he spits out a grape seed. They immediately take a dislike to each other.

Because they have a long trip ahead of them, Harry asks: "Why don't you tell me the story of your life?" Sally is a would-be journalist who is to "go to journalism school to become a reporter," and she wants to make a start in Manhattan. By contrast, Harry has "a dark side" and is obsessed with death, but Sally is "one of those cheerful people who dot their 'i's' with little hearts."

Harry: When I buy a new book, I always read the last page first. That way, in case I die before I finish, I know how it ends. That, my friend, is a dark side.
Sally: That doesn't mean you're deep or anything. I mean, yes, basically I'm a happy person...
Harry: So am I.
Sally: ...and I don't see that there's anything wrong with that.
Harry: Of course not. You're too busy being happy. Do you ever think about death?
Sally: Yes.
Harry: Sure you do. A fleeting thought that drifts in and out of the transom of your mind. I spend hours, I spend days...
Sally: - and you think this makes you a better person?
Harry: Look, when the s--t comes down, I'm gonna be prepared and you're not, that's all I'm saying.
Sally: And in the meantime, you're gonna ruin your whole life waiting for it.

As in Woody Allen's Play It Again, Sam (1972), the opinionated Harry is also obsessed with the film Casablanca (1942) and they argue about it (in voice-over) - expressing their two contrary perspectives about the film's finale. Her practical choice, later denied, is that she would prefer to leave with Victor Laszlo rather than stay with the self-sacrificing, romantic hero Rick (Humphrey Bogart):

Harry: He wants her to leave. That's why he puts her on the plane.
Sally: I don't think she wants to stay.
Harry: Of course she wants to stay. Wouldn't you rather be with Humphrey Bogart than the other guy?
Sally: I don't want to spend the rest of my life in Casablanca married to a man who runs a bar. That probably sounds very snobbish to you, but I don't.
Harry: You'd rather be in a passionless marriage -
Sally: - and be the First Lady of Czechoslovakia -
Harry: - than live with the man... you've had the greatest sex of your life with, just because he owns a bar and that is all he does.
Sally: Yes, and so would any woman in her right mind. Women are very practical. Even Ingrid Bergman, which is why she gets on the plane at the end of the movie.

As they enter a roadside cafe, Harry demonstrates his sexist and argumentative nature. Soon, Sally is debating the odds of having great sex with a guy named 'Sheldon' while they order a dinner meal. She is compulsively concerned about how her food should be prepared:

Harry: Obviously, you haven't had great sex yet...
Sally: It just so happens that I have had plenty of good sex... (Sally's infuriated response is so loud that other customers stop eating to notice her response.)
Harry: With whom did you have this great sex?
Sally: (embarrassed) I'm not going to tell you that!
Harry: Fine. Don't tell me.
Sally: Shel Gordon.
Harry: Shel. Sheldon? No, no. You did not have great sex with Sheldon.
Sally: I did too.
Harry: No, you didn't. A Sheldon can do your income taxes. If you need a root canal, Sheldon's your man, but humpin' and pumpin' is not Sheldon's strong suit. It's the name. 'Do it to me, Sheldon.' 'You're an animal, Sheldon.' 'Ride me, big Sheldon.' It doesn't work.
Waitress: What can I get you?
Sheldon: I'll have the Number Three.
Sally: I'd like the chef salad, please, with the oil and vinegar on the side. And the apple pie a la mode....But I'd like the pie heated, and I don't want the ice cream on top. I want it on the side. And I'd like strawberry instead of vanilla if you have it. If not, then no ice cream, just whipped cream, but only if it's real. If it's out of a can, then nothing.
Waitress: Not even the pie?
Sally: No, just the pie. But then not heated.

Curious about her relationship with Sheldon but also feigning disinterest, Harry pursues the issue further:

Harry: So how come you broke up with Sheldon?
Sally: How do you know we broke up?
Harry: Because if you didn't break up, you wouldn't be with me, you'd be off with Sheldon the Wonder Schlong.
Sally: First of all, I am not with you. And second of all, it is none of your business why we broke up.
Harry: You're right, you're right. I don't want to know.
Sally: Well, if you must know, it was because he was very jealous and I had these Days of the Week underpants.
Harry: (He makes a loud buzzer sound) I'm sorry. I need a judge's ruling on this. Days of the Week underpants?
Sally: Yes. They had the days of the week on them, and I thought they were sort of funny - and then one day, Sheldon says to me, 'You never wear Sunday.' He's all suspicious. Where was Sunday? Where had I left Sunday? And I told him, and he didn't believe me.
Harry: What?
Sally: They don't make Sunday.
Harry: Why not?
Sally: (matter-of-factly) Because of God.

After Sally has finished figuring out her portion of the bill and tip that she will pay, by using a calculator, Harry just stares at her and flirtatiously remarks how attractive she is:

Harry: (smiling) You're a very attractive person.
Sally: (suspicious) Thank you.
Harry: Amanda never said how attractive you were.
Sally: Well, maybe she doesn't think I'm attractive.
Harry: I don't think it's a matter of opinion. Empirically, you are attractive. (She gets up.)
Sally: (astonished) Amanda is my friend.
Harry: So?
Sally: So, you're going with her.
Harry: So?
Sally: So, you're coming on to me.
Harry: No I wasn't. (With disbelief, she stares at him.)

As they leave the diner, Sally defensively believes he is "coming on" to her. To carry his line of reasoning further - to get her riled up and to argue his point - Harry proposes going to bed with her. Ultimately, Harry believes that men and women cannot be friends, because sex will always interfere. [This is a classic discussion of the film's main question: "Can a man and a woman ever be 'just friends'"?]:

Harry: What? Can't a man say a woman is attractive without it being a come-on? All right, all right. Let's just say, just for the sake of argument, that it was a come-on. What do you want me to do about it? I take it back, OK? I take it back.
Sally: You can't take it back.
Harry: Why not?
Sally: Because it's already out there.
Harry: Oh jeez. What are we supposed to do? Call the cops? It's already out there!
Sally: Just let it lie, OK?
Harry: Great! Let it lie. That's my policy. (They get into the car.) That's what I always say. Let it lie. Want to spend the night in a motel? (She glares at him.) You see what I did? I didn't let it lie.
Sally: Harry -
Harry: I said I would and I didn't...I went the other way...What?
Sally: We are just going to be friends, OK?
Harry: Great, friends. It's the best thing...You realize, of course, that we can never be friends.
Sally: Why not?
Harry: What I'm saying is - and this is not a come-on in any way, shape, or form - is that men and women can't be friends, because the sex part always gets in the way.
Sally: That's not true. I have a number of men friends and there is no sex involved.
Harry: No, you don't.
Sally: Yes, I do.
Harry: No, you don't.
Sally: Yes, I do.
Harry: You only think you do.
Sally: You're saying I'm having sex with these men without my knowledge?
Harry: No, what I'm saying is they all want to have sex with you.
Sally: They do not.
Harry: Do too.
Sally: They do not.
Harry: Do too.
Sally: How do you know?
Harry: Because no man can be friends with a woman that he finds attractive. He always wants to have sex with her.
Sally: So you're saying that a man can be friends with a woman he finds unattractive.
Harry: No, you pretty much want to nail them, too.
Sally: What if they don't want to have sex with you?
Harry: Doesn't matter, because the sex thing is already out there, so the friendship is ultimately doomed, and that is the end of the story.
Sally: Well, I guess we're not gonna be friends, then.
Harry: Guess not.
Sally: That's too bad. You were the only person that I knew in New York.

The camera tracks their car as it crosses the George Washington Bridge into New York City, and they arrive at Harry's destination near Washington Square. In an awkward moment of goodbye, they shake hands and part ways after an "interesting" ride:

Harry: It was nice knowin' ya.
Sally: Yeah. (They shake hands - and she waves. After walking to the car door, she turns.) Well, have a nice life.
Harry: You too.

As an interlude, a second direct-camera interview is presented, with an even older couple sitting together on the same loveseat:

Woman: We fell in love in high school.
Man: Yeah, we were high school sweethearts.
Woman: But then after our junior year, his parents moved away.
Man: But I never forgot her.
Woman: He never forgot me.
Man: No, her face was burned on my brain. And it was thirty-four years later that I was walking down Broadway and I saw her come out of Toffinetti's.
Woman: And we both looked at each other, and it was just as though not a single day had gone by.
Man: She was just as beautiful as she was at sixteen.
Woman: He was just the same. He looked exactly the same.

FIVE YEARS LATER

At La Guardia Airport in New York, another loving couple are kissing at one of the departure gates. Sally and her new boyfriend named Joe (Steven Ford). When Harry, now wearing a suit and tie, passes by the couple to catch a plane to Washington, he notices them, goes past, and then backs up. Joe, a lawyer, is an acquaintance of Harry's, who has become a political consultant. Although he greets Joe, Harry is unable to place Sally in his memory, but he looks quizzically at her after being introduced. When Harry boards the plane, she tells Joe about her distasteful memories of their college-era drive to New York:

Sally: Thank God he couldn't place me. I drove from college to New York with him five years ago and it was the longest night of my life...He made a pass at me, and when I said no - he was going with a girlfriend of mine - oh God, I can't remember her name. (jokingly) Don't get involved with me, Joe, I am twenty-six years old and I can't even remember the name of the girl I was such good friends with, I wouldn't get involved with her boyfriend...I said we could just be friends, and - this part I remember - he said that men and women could never really be friends. Do you think that's true?
Joe: No.
Sally: Do you have any woman friends, just friends?
Joe: No, but I will get one if it's important to you.

Finding themselves on the same plane and only one row apart, Harry overhears Sally's fussy ordering, and then suddenly places her: "The University of Chicago, right?" They renew acquaintances after he switches seats to be next to her. Both of them are in relationships - Sally has only known Joe for a month and she tells Harry: "Neither one of us is looking to get married right now." On the contrary, Harry, a crude and cynical womanizer who is "madly in love", is "embracing life" (according to Sally) and getting married to Helen Hillson, a lawyer:

Harry: ...You just get to a certain point when you get tired of the whole thing.
Sally: What whole thing?
Harry: The whole life-of-a-single-guy. You meet someone, you have the safe lunch, you decide you like each other enough to move on to dinner, you go dancing, you do the white man's overbite, you go back to her place, you have sex, and the minute you're finished, you know what goes through your mind? How long do I have to lie here and hold her before I can get up and go home? Is thirty seconds enough?
Sally: That's what you're thinking? Is that true?
Harry: Sure. All men think that. How long do you like to be held afterwards? All night, right? See, that's the problem. Somewhere between thirty seconds and all night is your problem.
Sally: I don't have a problem.
Harry: Yeah, you do.

While staying over in Washington, Harry proposes that they both have dinner together - as friends. As they stood on the moving escalator at the airport, he struggles to explain that he has an amendment to his earlier rule about relationships between men and women:

Yes, that's right. They can't be friends...unless both of them are involved with other people. Then they can. This is an amendment to the earlier rule. If the two people are in relationships, the pressure of possible involvement is lifted. That doesn't work either. Because what happens then is the person you're involved with can't understand why you need to be friends with the person you're just friends with, like it means something is missing from the relationship and wanted to go outside to get it. Then when you say, 'No, no, no, no, it's not true, nothing is missing from the relationship,' the person you're involved with then accuses you of being secretly attracted to the person you're just friends with, which you probably are - I mean, come on, who the hell are we kidding, let's face it - which brings us back to the earlier rule before the amendment, which is men and women can't be friends. So where does it leave us?

They both realize that they must not see each other and part ways again.