You Should Date Whomever The Hell You Want
When you’re filling out an online dating profile or at one of those awful speed dating events (which I have never frequented, obviously), you are often asked what “kind of guy” you’re looking for, as if you’re picking out a puppy at a pound. Do you want a Black Laborador guy — the kind of guy who is sleek, smooth and goes with everything — or a Corgi, fun and cute, with a lot of character? Or do you want a Basset Hound man — someone who comes with a bit of mileage but is dependable? While you’re at it, would you like your dating life spayed or neutered?
It’s the first thing you’re ever asked when you’re set up: “So, what are you looking for? What’s your type?” You are then supposed to offer up some magical indicator of what kind of person you are and what you want in the world by uttering a random combination of the words “tall,” “dark,” “handsome,” “owns stock in Apple” or “lives at Chipotle,” and this will automatically register a response in the asker’s brain. “Oh, you want someone with legs and hands? Great, I know a million people to set you up with.”
This is pointless because a) that person was always going to set you up with the person they had in mind, anyway, so you could say you’re looking for a serial killer with great taste in knives and it doesn’t matter and b) types are bullshit.
There’s a common Latin proverb that reads “Cite Vos,” translating to “Know Yourself.” This has two meanings, and the first is simple: As a person, you should get in touch with who you actually are — not the person you are for other people or the one you project. Notice that they didn’t say “Know Your Dating Life,” because no matter how old you are, that won’t change. You might be a little older and wiser when you’re 50, but love will be a mystery to you for the rest of your life. The opposite sex won’t get easier to understand, and you still won’t know what they’re thinking.
But isn’t that what’s great about it? As you get older, figuring out who you are means being comfortable with the things you can’t control — the mysteries of the universe. They say that true intelligence is being able to say “I don’t know,” so why aren’t more of us dating smart? Why aren’t we able to admit that we don’t know want? The moment you actually start dating, most of the things you thought would be dealbreakers when you were young get thrown out the window, anyway. The things you think you want won’t be important. Instead, you’ll discover what you actually need.
How can you figure that out if you only date one type of person for the rest of your life? Doesn’t that sound horribly boring? I love avocados. Avocados are my favorite food. But if someone forced me to only eat avocados — to never wander out and try anything other than the thing I already know I like — I would go insane. I used to be the kind of person who was comfortable ordering the same meal at a restaurant every time I went there. If you already know what you want, why experiment? What if you order something that sucks?
One day I was at a burger joint with a friend in the South Loop and I got my usual: A turkey burger and fries — with a side of mayo. Noticing that in our entire friendship I had never gotten anything else, she asked me about it, and I related my apprehension to eating things I don’t like. She responded back, right away, “But what’s wrong with having a bad meal every once in a while? Sometimes you just have to do something different, and if it’s not great, who cares? You just have to let the food be bad.”
We do this in a million different ways, sticking to what’s familiar and comfortable because we’re too nervous to take chances. What’s different is scary — but it doesn’t have to be. Every day most aspects of your life are different. You might take the same train to work, but few of the people you see will be the same ones you saw yesterday. The conversations around you will be different, and even if you’ve been in a relationship for years, the sex will be different, even if it feels the same. Every day is an invitation to newness, just as long as you’re willing to accept it.
In life, you’re often told to seize the day, but I want you to seize the multitudes. I want you to get out there and try a lot of different things. Take jobs you are blatantly not qualified for and hope for the best. See a movie you’ve never heard of. Fly somewhere you’ve never been — just to get away. Take the train and ride around the city without a destination, ready to see things you’ve never seen before. Go out with that person you don’t think you’re that interested in and let him surprise you. Don’t be afraid to let life surprise you.
There’s another definition to “Cite Vos,” one that people neglect. Part of knowing yourself is defining yourself, being an active agent in the shaping of your own existence. The idea is that you shouldn’t listen to the will of the mass and that you should be a light unto yourself. This means that if you really want to know yourself, you should stop listening to other people’s advice so much and take a little or your own.
We get so used to other people’s advice that we forget to listen to our own hearts — or better yet, make it up along the way. We forget that half of life is the fun of figuring it out, fucking up royally and hoping to do better next time.
I think the first rule of a dating columnist shouldn’t be to tell you who to date — whether that’s someone “who doesn’t do social media” or someone “who doesn’t love you.” Date whoever the fuck you want, because you are going to anyway. You’re going to date some huge fucking losers and go on dates you’ll laugh about later. You’ll have other dates that are so bad you go home and cry later, believing you could never go out with anyone again and are doomed to die alone, half eaten by wild dogs.
You’ll also have dates that restore your faith in humanity. They’ll challenge you with interesting conversation, forcing you to consider new ideas. You will date people who won’t grow old with you but will push you to be a more interesting person, and even if they dump you in a terrible way, it’s a great story. Always remember: No matter how bad things get, you’ll survive and live to tell the tale. And it’s the telling that makes life worth living.
So date a total jerk who won’t let you meet his mom. Date someone who doesn’t have time for you and then dump him for someone who lets you stay over and holds you all night. Date someone who doesn’t return your calls and then get too good for him and stop calling. Date someone you asked out first and someone who is okay with being asked out or with you paying for the first date. Date someone who doesn’t love you and learn that you deserve more.
Date all kinds of people — because you’ll never know what you like until you find out what you don’t. Just don’t be afraid to make mistakes and get messy along the way. No one ever got to where they were because they did anything perfectly. Perfection is fine, but it’s the beautiful imperfections that make you who you are. 
