THE BLOG
07/22/2015 04:05 pm ET Updated Jul 20, 2016

Are You a Simple or Complicated Person?

My favorite scene from When Harry Meets Sally isn't the famous orgasm "I'll have what she's having" scene or when Harry declares his love for Sally at the end on New Year's Eve. Instead it's the scene where Harry explains that there are two types of women in the world: high maintenance and low maintenance. Sally asks which type she is and Harry replies that she is the worst kind - the kind that thinks they're low maintenance, but really is high maintenance.

This quote kicked off a long conversation with probably the one person in the world who knows me best in some twisted way - a friend I've been close with since middle school that became my first boyfriend and the first person to break my heart, but now is one of my best friends. You know that guy? Everybody has some version of that guy. It's the guy where if our lives were a romantic comedy, we would end up together after both dating other people for ten years and meeting at our high school reunion or over Christmas when we're both back home and running into each other's arms in the perfectly drifting snow. Except this is the real world and life doesn't happen that way. Thank goodness.

Anyways, instead of high or low maintenance, we discussed if we were simple or complicated people. When we were both still in college and just hanging out in his car one night over bobba tea (we're from Cupertino, California - this is what people do!), he told me that he knew his future wife would be a complicated girl. Fast forward to med school for him and business school for me, our most recent conversation led to him laughing, "No, I was an idiot. Complicated people are so...difficult. I'm glad my current girlfriend and I are easy and simple. We're just... good."

I am a complicated girl or as Sex and the City coined it, a "Katie girl" after Barbra Streisand's character in The Way We Were. And I don't say that with particular pride as if being complicated is better. Sometimes I wish I could shut off my brain from over analyzing things and can only imagine how much easier my life would be if I were more simple. I've seen my male friends date girls I always called "sweet" girls (and somehow always named Sarah) and they seem perfectly lovely, if only a little bit dull. In the most self-centered text I have ever sent and only possible to someone you're that good of friends with, I texted him today and asked, "Okay, if I'm a complicated girl, then should I date a simple guy or a complicated guy?" He responded by explaining his philosophy that life is like Gossip Girl. Do you want to be in a Blair/Chuck relationship or a Serena/Nate relationship? Like I said, we were never ever going to work out.

But in some way, I think he's right. As I see more and more people getting engaged and married, the theme I've noticed is that the ones who are getting married now have simple relationships. I'm not saying their love is easy or less passionate, it's just that their relationships don't have a lot of clutter and no one has a lot of baggage. They've been together for so long that they are each other's past and no one has to deal with the ramifications of the hurt caused by someone else before them. And not just the distrust and insecurities from past relationships, but from anything in their past. Ask anybody who has dated someone with something as basic as physical insecurities or family drama and you will know how much it can affect a relationship because it's just such a large part of who they are. Very few people out there are just that wholesome.

My friend's point at the end was that if you date a complicated guy, things will be more difficult, but he might understand you better, while things might be easy with a simple guy, but you'll be frustrated when he doesn't seem to get you. At the end of the day, I've always believed that everyone is crazy. You just need to find someone whose crazy matches your crazy and whose baggage matches your baggage. And even if you don't find this crazy person, it's okay, there are a lot of other crazy people out there that make pretty good friends.