The hierarchy of failure

Dave Gutteridge
6 min readOct 18, 2019
Sillhouette of a father and child on a beach

I’m talking to my friend. Friend? She’s more like an acquaintance, because we don’t really hang out that much. She’s pretty hot, and I’d kind of like to have sex with her, and I think she kind of knows that, because she flatters me in this strange way where I wonder if she’s trying to manipulate me. I don’t think sex is going to happen, though, and that’s fine.

There was a time when I was more keen to have sex with her, back when my sexual desire made me less able to see more fundamental incompatibilities. Although, over the course of my life, I have managed to get into long relationships in spite of retrospectively obvious differences, so who knows what might have been possible. In any case, I took her on a date one time, but that’s as far as it got.

That was about twenty years ago, and at the time, she was clearly pursuing a very different type of guy than me. She wanted someone richer, more career driven, the kind of business suit wearing guy that you had no questions about whether or not they could buy a house in the next few years. Definitely not me.

This wasn’t just a theoretical list of qualities in an ideal mate that I was projecting onto her. She told me one time back then, in a conversation that for some reason I clearly remember happening on a street corner in Omotesando where we must have randomly bumped into each other, that she had made a list of specific objectives for her life. She wanted to achieve certain career goals within period of time, get married and have kids within a specific age range, and she had a list of characteristics that she wanted in a potential partner.

She was very driven, the type who reads books about how to self actualize and achieve in life and that sort of thing. Even though I disagreed with the strategy of writing a concrete timeline for one’s life to the degree that it precludes a certain amount of unanticipated opportunity, I respected her overall proactivity in making something happen for herself. She wasn’t just receiving life, she was engaging it, directing it, trying to make the most of it.

Twenty years later, I’m listening to her unload because she’s getting a divorce, certain business opportunities are going off the rails, and a lot of bottled up emotions are coming out. I’m not a confidant of hers or anything. We’ve barely kept…

Dave Gutteridge

I write thought-provoking pieces on ethics, relationships, and philosophy with honesty and vulnerability, often inspired by experiences and pop culture.