Everything I've learned about women, I learned from When Harry Met Sally

This week I watched When Harry Met Sally. I haven’t seen the film in about 20 years, and since I have plenty of time right now while I’m recovering from shoulder surgery, movies get to occupy more time. Seeing this appear on Netflix’s New Release menu, it was like the stars aligning.

And boy what a great decision that was! The biggest reason being, it should be no surprise that my perspective has matured, or at least changed, in 20 years. I appreciate this movie so much more now that I have an additional 20 years under my belt. The movie is richer and altogether ever more enjoyable. In addition to this, and probably a bit more important, there are a lot of great jokes; jokes which I’m certain I totally missed the first time I saw it. One in particular is,

Harry: So I down shift into small talk, and I asked her where she went to school and she said. “Michigan State”, and this reminds me of Helen. All of a sudden I’m in the middle of this mess of an anxiety attack, my heart is beating like a wild man and I start sweating like a pig.

Sally: Helen went to Michigan State?

Harry: No she went to Northwestern, but they’re both big-ten schools. I got so upset I had to leave the restaurant.

Big laughs from this line just because of the lengths his mind went through to make this association! This also tells us a bit about Harry we don’t really know to this point: he is a big sports fan! The joke is so funny because it’s so rich and subtle. It’s probably my favorite joke in the film.

Great jokes aside, this is not the reason I’m writing about this. As I watched the film again, a great realization dawned on me… everything I’ve learned about women, relationships, and romance came from When Harry Met Sally. There are three main points in the movie that have shaped my worldview in the area of estrogen and my attempts to be around it.

1. No man can be friends with a woman that he finds attractive. He always wants to have sex with her.

When I saw this as a 14-year-old boy I probably laughed because I thought Billy Crystal was funny. I still think he’s funny, but when I heard this again I had an epiphany. A young man, a photographer, wrote an email to a Chabad rabbi in which he said he spends all day with beautiful women and never wants to have sex with them. The rabbi replied, “You’re broken!”

Until this moment, I thought that this view was a conservative religious viewpoint. But, after hearing Harry say this to Sally I realized that it was an old memory that had been recycled into my modern choice of life. The good news about this is that this viewpoint is not only held by religious conservatives. It is a very practical, and informed way to view how a man relates to a woman. Maybe you think I’m being shallow and misogynistic, but let me tell you that men think about sex. A lot. And if for some reason a man is not thinking about sex, just give him a few minutes and it will cross his mind again.

I think that it is very important for us to accept this fact and just move on. Thinking this way can keep us out of a lot of trouble! Guys, if you’re with a woman you love, there’s no reason you want to spend significant time with another woman unless you have an ulterior motive. Guys, you can say you’re just friends, but any length of time you’re spending with a woman will yield sexual desire—we’re just made that way. So unless you want to ruin a good thing, stay away from other women. It’s like driving a car… sure, you’re a good driver, but sooner or later, you’re going to get banged, up in an accident that is.

Women, this applies to you too. Men really do think about sex almost all of the time. Maybe it is platonic, but sooner or later, sex will rear its head in that friendship. It will. It just will. Accept it. It doesn’t mean you’ll do it, but it will be there. Always. Just waiting to surface.

But what about unattractive women? Sally asked the same question. Harry replied, “Nope. You pretty much want to nail them too.”

No one is safe. Grrrrowwwlll

2. There are two kinds of women: high maintenance and low maintenance.

Fellas (and ladies in denial), there are only two types of women. I do imagine that this either/or scale is relative according to means, patience, and desire. Regardless, you will find women who are easy to take care of, and those who require a lot of attention. It’s the difference between driving… aw hell, I don’t know enough about cars to make a comparison, so fill in your own metaphor. But what is low and high maintenance?

A low maintenance woman is someone who is easy-going and relaxed. You aren’t going to be running around like a chicken with your head cut off to make her happy every day. You’re not going to be stressing about how to get her to relax. You’re also not going to have a lot of fashion and home modeling magazines lying around your house for casual reading. You know those magazines are only going to give her ideas that are going to make your honey-do list grow exponentially. I had a friend whose wife made him redesign their house every 2–3 years. I am not a handy man. I would not only have been incapable of completing the work in a timely manner, but I would have been very cranky while doing so.

To know what a high maintenance woman is, just reread the previous paragraph. She’s like the low-maintenance woman, just more difficult. Here’s some advice: if you don’t have the salary or general patience to tolerate a high maintenance woman, just stay away. The first whiff you get of this type, and you’re not able to handle it, just call it quits. There is no shame in this! Everyone will be happier in the long run. Kiss her cheek, kiss her hand, and bid her a good night. You will thank me for this later… or you’ll tell me I was right. Either way, you have to be prepared to meet her and know how to respond. The high maintenance woman will drive you insane if you’re not built to handle her.

3. What are you saying, that they fake orgasm?

What? Fake? You mean? Ugh. How will my fragile man-ego handle this shattering blow? I thought I was God’s gift to women, a veritable modern-day Casanova! This news is shattering.

Okay, so now you know the truth, and you have some choices to make. The first is the easiest: If you’re married, you better be damn sure you’re taking care of your wife’s needs. You’d better be making sure that communication is open and honest enough to do what you need to do for her to show you her “O-face”. Some men are gifted with wives who orgasm at the drop of a hat. I don’t know any of them. Others… well, put your big boy pants on (or take them off in this case) and get ready to enter a marathon. Men, we take pride in the work we do at our jobs and the things we create. Don’t slack in the bedroom because this will bring down your abilities in all other areas of your life. There’s nothing more satisfying than bringing your wife to authentic orgasm. And if you’re not doing it, chances are you’ll be living with a really tense, unpleasant woman after a while. What would you be like if you always ended up with blue balls post-coitus?

For you single guys… you have a few variables that complicate this process. Are you in a steady relationship? If yes, then see married above. Are you just dating, friends with benefits, or just hooking up when you can? What’s your attitude in general? Do you want to leave the woman with a favorable impression of you? If it’s yes, then see married. Work your ass off and make sure you’ve done all you can so if she’s faking it, it’s because she knows you’re getting tired. Or, just go with the old joke, “How long does it take the average woman to orgasm? Who cares.” But it’s not a race, fellas. Take it easy off the starting line. But in the end, you won’t know if she faked it or not. If you care, the least you can do is give little room for doubt.

What about men faking orgasm? I’ve tried it and it never worked for me. The couple of times I tried it she knew. Don’t waste your time. If it’s that bad… well, you’re on your own there. I got nothing for you in this arena.

Wrapping it up

This movie shaped my modern view of relationships more than I knew. It probably did this for several of my generation. The jokes are great, the budding romance between Harry and Sally is sweet and creates such tension that you can’t wait to get to the end. They were so good on the screen together and so believable. How could you not learn something from this timeless classic? So now that you’ve read this, go watch it again, and then apply these lessons if you haven’t already. You’ll make your world a better place… and probably your woman’s too.

And as I wrap this up, another realization dawns on me… is my perception of relationships so shallow that it is defined in a 90-minute movie made in 1989? Or am I, as a man, only concerned about the sexual aspect of the relationship and what it’s going to require of me to keep the sex regular and good? Or, as long as everyone’s happy, does it really matter?

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