You Should Date A Man Who’s Difficult


I want to date someone difficult. I openly admit it. I’ve noticed that there is one thing all my successful friends have in common: successful people have an ability to take on difficult tasks, difficult people, and difficult situations. The common denominator here is “difficult.” It has everything to do with high standards, high expectations, and feeling disappointed when one falls short. As much as I like to think that I can be my best self without the pressures and fear behind the anxious lurking of failure, basic human psychology—and my own experience—has taught me otherwise.

My longest relationship was with a very difficult person. Granted, it was when I was 19, but he pushed me towards the outer limits of myself intellectually. He was a grouch and he was a nerd. He was difficult to be with because he was sensitive and intelligent. He was demanding, because it seemed like he could never be stimulated enough intellectually, and I was constantly aware that I had to be up-to-date with the latest books (or at least making my way through the classics) lest he suddenly find me boring.

I wanted to win him over. I admit it, I wanted to please him, and I was far too flattered when he said that I was the only woman who he thought was his intellectual equal. He probably shouldn’t have said that because it’s mean to other women. But he was being honest and difficult. His expectations are high. As a woman who tries hard to be a feminist, is it a bad thing that I only pushed myself to be a better version than I would have been alone, sitting in my room, afraid of the world and reading the occasional Jane Austen novel because of a smart boy? Maybe. But worse things have happened. And don’t we always want to please our significant others? Isn’t Facebook just a giant page for people-pleasing? Is it wrong to want to meet the high expectations of one single person as opposed to many?

It wasn’t the happiest relationship of my life, but he fucking kept me on my toes like no one else has been capable of doing since afterwards. And if it sounds like my admiration of him led to him to walking all over me, you’d be wrong to think that. He taught me to stand up for myself because he simply could not accept what fell beneath his standards. By holding me to his high expectations, he allowed me to rise up to them.

Once, when I was afraid to ask a professor for a letter of recommendation, waiting in agony for at least 30 minutes outside of his office as my ex-boyfriend sat outside with me on a bench, he eventually gave up on patiently waiting, and with a pained and slightly scornful expression on his face, told me to just go do it. That stuck with me. When I find myself in similar situations, I don’t imagine to myself, as other girls might, a kind and gentle voice telling me it’s ok, or a man who will walk in there and do it for me. Instead, I toughen myself up and I think, “Just do it!” Although it may seem harsh, sometimes people need to be pushed to unleash that part of themselves they wouldn’t have access to otherwise.

When we broke up, I later heard through a friend he said that I was “too romantic.” And in this he was right, too, I eventually realized. I was. I was too idealistic, and my expectations were too high, and—here the truth has to come out—I’m a difficult person as well.

I want people to be kind and smart and sensitive and funny, ALL THE TIME. Especially the kindness part. Is that too much to ask for? Yes. No one is perfect and no one can or should be kind, all the time. I agree that I should be more practical and realistic, and less like a delicate flower of a woman from the 19th century. I accept the criticism that I am “too romantic” and have been mulling over what this means, and working on it. But I disagree with you that that was something you found to be a flaw in me, ex-boyfriend. You loved it that I was too romantic. You loved it that I was difficult. You loved it that I gave you shit for not being kinder and a stronger person so that I could depend on, because it pushed you to understand me better, it pushed you to be a more considerate and kinder person, and it pushed you to think about where you were taking your life.

Maybe I won’t choose entirely difficult people as my significant others for my entire life. It’s not easy, and I’m more about balance than I am about extremes. I dislike thinking in blacks and whites. I think that there needs to be equal parts fear and failure, and equal parts calm, happiness, contentment, and success. I do think that slight pressure needs to be there though, even if this makes people and relationships so much more complicated. If I had to make my choice between a nice guy or a difficult guy, though, I’d choose the difficult guy every time. In the end, he pushed me too hard, but he brought me further than I ever would have come on my own. We talked for hours about books, we exchanged writing, we competed with each other in classes, we psychoanalyzed each other, we fought, and became smarter and better for it. I used our conversations, our thoughts, and ideas we exchanged in my personal statement for Harvard. And I was accepted.

So, difficult person, thank you. I may still be too romantic and emotional, as you pointed out, and you may be the more logical one (and ignore your emotions completely) but I’m working on it. I am. And I can’t wait to see what exciting places this new discovery brings me in the future, too. Perhaps a greater capacity for work and less stress in my life. I welcome the challenge. We’ll see.