There are some relationships that don’t work out because of small incompatibilities: you want to settle down in different places, he hates your cat, she’s geographically undesirable.

Then, there are relationships that don’t work out because they are complete, total, abject disasters, and that’s the kind I would like to tell you about today.

Before I met my now-fiancé, I dated a guy that I’m not necessarily proud of. To be fair, the issues that made Ben* such unfortunate boyfriend material weren’t really his fault; they included but were not limited to severe bipolar disorder for which he took medication only sporadically, the fact that he was only 20 years old to my 25, and his on-again-off-again homelessness.

Let me first defend myself by saying that no, we did not lock eyes and fall in love following his mumbled request for a cigarette as I walked past him on Hollywood Blvd. When our paths first crossed, Ben was staying with a friend of mine and building the set for a play that her husband was directing.

You see, he was an artist.

The night after we met, we began what I thought would be a quick fling. After his gig was over, I figured he’d either find his own place to live in LA or move back to the Bay area where he was from, and our affair would happily and easily fizzle out and die.

I was wrong. After the play wrapped, Ben thought out his next move, and through logical reasoning, determined that it would be to move into his car. While some may have called that a dealbreaker, I called it a project.

I coaxed and cajoled him to get a job; I helped him figure out how to use Craigslist to find an apartment, and forced him into a neighborhood that I liked. I’d like to say that my “helpfulness” sprang from a well of deep, abiding love, but it didn’t. It sprang from my own contributions to the fucked-up nature of the relationship: namely, my insistence on fixing every man that I met, and the overwhelming guilt I felt over the possibility of abandoning someone who seemed so fragile. (These would later be worked out in therapy.)

Over the course of what wound up being an eight-month relationship, our problems escalated. He could hardly ever go out with me, because he was underage, which was nothing short of humiliating since my friends and I had all been out of college for at least four years. When his bipolar disorder flared up, he either went on manic rants or smoked enough weed to put to sleep all present and former recording artists on Death Row Records. And my inability to cut the chord left me with increasingly pent up rage that came out in what I will euphemistically call “unbecoming,” extremely passive-aggressive ways.

Ben eventually let me off the hook when he decided that in order to reach his full potential, he had to go work on a fishing boat off the coast of Alaska. One sunny afternoon in August, he got in his pick-up truck and headed out for the wild blue yonder.

Several weeks later, he called to tell me that he had failed the drug test administered by the fishing boat company. Romantic ending, isn’t it?

*All names have been changed. Except mine. It’s too late for that kind of modesty.