Casual Encounters: Part 3 of a History With Relationship OCD

Part 1 | Part 2

During this writing I found out that the Internet Archive captured my OkCupid dating profile from 2009, right before I met Damien. Here’s a snippet of how I presented myself to the twentysomething men of Portland.

My Self-Summary: I'm a fairly normal, down-to-earth kind of person. My default state is generally calm and cerebral, but I love to be silly when in the right company. I'm an observer who typically appears to be lost in thought (because I usually am).

What I’m doing with my life: Trying to stay active, entertained, curious, and creative. Searching for a sense of purpose and passion in my life. I'm okay with the fact that I haven't found it yet—there will always be more to learn.

You should message me if: You're smart, irreverent, generally polite, down-to-earth, and at least a little bit nerdy. You don't mind hanging around somebody who is shy and dorky (not always the former, but usually the latter). You're not a big partier. You realize that life is short and the world is often intensely beautiful.

I reactivated it after I’d recovered enough from the Damien breakup. The recovery involved chopping my hair off to shoulder length and adopting two cats. I also moved into a nicer apartment that would let me keep said pets. My life was going well, but I still wanted to be coupled up with a geeky, bike-riding, cat aficionado. Browsing OkCupid and getting messages from new prospects was like taking samples at a dopamine factory. Any time I worried that there wasn’t somebody for me, I just logged in to indulge in fantasies about the people behind the profiles. It was easy to gin up a sense of yearning based on an attractive photo, a witty exchange, or a line in their bio that convinced me we would get along. In other words, it was easy to build up expectations. Meeting online dates in the flesh always required a small readjustment of those expectations. Once I broke through that first little shock, most of the men I dated turned out to be perfectly fine, if not love matches.

A handful of dates turned into relationships that lasted a month or longer, but it was a struggle to get to there. Usually I couldn’t make up my mind about whether I wanted to see them again, and so erred on the side of not. I dropped many like hot potatoes, particularly the ones who showed a keen interest in me. That was too scary, too risky. I’m sure that I missed out on getting to know some interesting men. There was one who packed us a picnic lunch and biked 20 miles with me out to Sauvie Island, riding country roads in a light rain. There was another one who took me to a Loudon Wainwright III concert. I said no to both when they asked me out again. With the ones I decided to continue seeing, I ran into the familiar issues of overthinking, chronic worrying, and—this was clear by now—fear of intimacy. It seemed that I wasn’t destined for a long term relationship.

I started to get bitter before I turned thirty, scowling inwardly at happy couples I saw in public. I privately resented friends who settled down with partners, and semi-publicly lamented on Facebook that I would never find anyone. I felt impossible to love, and believed it was my own fault for being unable to just stop the overthinking. I was seeing therapists, but found it hard to make meaningful progress with them. We focused a lot on my generalized anxiety disorder, my perfectionism, and the origins of my poor sense of self worth, but just kind of went around in circles, rehashing the principles of cognitive behavioral therapy. It wasn’t unhelpful, but I think it lacked a focus on the obsessiveness of it all. Maybe the notion of OCD affecting someone’s emotional life wasn’t really on the radar then. I occasionally felt like I was wasting my therapists’ and my time. I actually stopped seeing one counselor because she was from New York, wore leather, and had treated patients with serious issues like drug addiction—how could she possibly take my problems seriously? I was just one of many Women Who Think Too Much, which was the title of a book that my best friend recommended because she saw my suffering and thought it might help. It sounded like a B-movie parody.


Since I wasn’t getting better, I decided to change tack and forget about love for a while. I updated my OkCupid profile to “looking for casual sex” and started posting on the Craiglist “casual encounters” board. It was new territory for this Pollyanna, but seemed like a fun way to get some validation and a warm body next to me. Being a single woman online looking for NSA (no strings attached) hookups is very lucrative. I had to set up an inbox rule to filter all the emails from Craigslist. I made my own personal rules too. If a guy sent me an unsolicited photo of their junk, it went straight into the trash. They had to write with reasonable grammar and spelling, and we had to meet for a date before sleeping together. If something felt a little off during the date, or if there was no chemistry and I couldn’t picture myself naked with them, I wouldn’t take them home.

I couldn’t tell you what my rate of success was, but I ended up with a good share of one- or two-night stands. We usually met at some dark bar in my neighborhood off Southeast Division Street and made cursory small talk while sizing each other up. Okay, I was sizing them up. I’m not sure any of them would have turned me down. I was fit, curvy, willing, and I lived nearby. If we got along well, sometimes we’d hang out and listen to music in my living room either before or after having sex, which by itself was generally nothing special. It was an hour of fun (mostly for the man, ahem) and companionship, followed by them leaving me alone, which I thought I preferred.

It was a weird time in my life. Casual hookups weren’t something that came very naturally to me, but they was an opportunity to suspend all expectations. My brain didn’t need to evaluate these partners for long term viability; all I had to do was offer them a very clear value proposition, unpolluted by emotional needs. It made dating a little more simple and enjoyable. I slept with a divorced dad after we went to Laser Floyd and made out in the planetarium. I had a few trysts with an attorney, also a divorced dad, who liked to talked about music and introduced me to some great bands. And there was a music-industry guy, a producer or something, whom I got a crush on despite my best efforts. He was the most aloof out of all of them, telling me nothing personal about himself that I recall. I’m sure I was attracted to the “hard to get” aspect. He stopped responding to my texts when they stopped being about booty calls.

Reed was the one of the rare hookups that turned into a sustained fling. We met through Craigslist, hit it off, and continued seeing each other long enough that some of my friends started to give it the side eye. He found me attractive and interesting as a whole person, and lifted me up when I was too self deprecating about my romantic failures. He was relaxed where I was uptight; I even smoked weed with him, which I had never done before. (See? Pollyanna.) Still I didn’t think he was right for me in the long-term sense, and he had no expectations either. It was the most trouble-free relationship I’d ever had. My therapist at the time probed me to look at why that was. I knew myself well enough that I didn’t have to dig far—this was easy because there was nothing at stake, because it was not “serious”. I had, over time and subconsciously, built up a whole closetful of expectations about what a serious relationship should be. Since I wasn’t asking Reed to fulfill any of those, I could just enjoy being with him.

I realized I’d been through a micro version of that in previous failed relationships. After OCD compelled me to break up with someone, I was so uncertain about the decision that I usually left the door open for them to hang out and/or have sex with me, which most of them eagerly used. I relaxed during those encounters because, technically, we were broken up. No future = no risk = no worry. On the flip side, I’d be fooled into thinking we could get back together and it would be easy this time. But it never turned out that way. Putting a commitment around something, even if it wasn’t explicitly stated, automatically put me back into obsessive mode.

Reed and I continued seeing each other intermittently for a year or so, while I carried on with a few other hookups. At some point I got tired of suppressing my romantic side. Even Reed encouraged me to look for someone who fulfilled me in all ways. Being with him re-energized me and restored some faith that men could want me for more than sex. I am still fond of him, years after we’ve both settled down with our people.