Mistakes Were Made: A Guide to My Previous Relationships and Significant Romantic Attractions, and What Went Wrong

by dpreyde

I thought this would make a nice appendix for the dating guide, which of course is ongoing.

Before I get into this, I feel I should note that all names have been changed, as well as some identifying characteristics.

Kelly Flynn: 1994-1996, 1998-2000

What was the deal?: We met in grade two and became best friends almost immediately. We both caught hell from our other friends, because I was a boy and she was a girl, and don’t you know boys/girls have cooties? We got married in a sandbox ceremony during recess in grade two. In grade three we got divorced after she punched me in the mouth on school photo day. Three years later, in grade six, we became friends again. I had spectacularly poor judgment and rock-bottom emotional intelligence, and didn’t believe in diplomacy, selflessness, or basic human decency. She had a hair-trigger temper and no impulse control. It was a match made in paradise.

What went wrong?: We were twelve. She recognized that fact, while I wanted to be with her forever. She explained to me that it wasn’t going to work, I internalized my resentment and took it out on her over the next few months. She gave as good as she got. Eventually we called a truce and were able to remain friends.

The lesson learned: Don’t be an asshole.

Naomi Dickson: 2000

What was the deal?: In July 2000, shortly after my thirteenth birthday, my family got the Internet. Because I had poor judgment I immediately started frequenting a teen chat room on a regular basis. It was there that I struck up a friendship with Naomi Dickson. She was a Scouser who was fourteen going on thirty. She drank to excess, played sick pranks for fun, and had the dirtiest sense of humour out of anyone I’ve ever met. We started dating almost right away, and right away, I was way over my head. She was my first girlfriend.

What went wrong?: We moved too fast. Both of us had serious impulse control problems. A week after meeting, we were talking about getting married someday. Three weeks after we met, we broke up. It was actually completely cordial; we simply recognized we weren’t a good match. We were close friends for years afterward.

The lesson learned: Nothing about dating has to be painful or complicated. You can have a relationship on a whim if that’s what you want. You can break up just as easy. Nobody ever has to be the bad guy.

Caitlin Hood: 2000-2001

What was the deal?: I met Caitlin online. She was another regular on the teen chat room, and lived in the southern United States. Unlike Naomi, she was preppy, and prided herself on maintaining a good-girl image. We dated on and off for several months. It was an unmitigated disaster.

What went wrong?: Our relationship occurred at the tail-end of what I like to call “The Bastard Years” in which I was a bastard to everyone I cared about. My emotional intelligence was low, I had bad impulse control, and was frequently viciously angry. I didn’t trust her, and often felt manipulated. I have no idea whether these feelings were justified- as noted, I was a bit of a mess at the time.

The lesson learned: This is one of those relationships which I think is good to have when you’re young. You and your partner make every mistake it’s possible to make, you really fuck each other up, you get your feelings hurt a lot, and then you move on and never find yourself in a similar situation again.

As a side note, I feel I should emphasize the subjectivty of my experiences. I’ve talked with Caitlin a few times over the years about our relationship, and she remembers that period fondly and with great nostalgia.

Joanna Macintosh: 2001-2003, 2004

What was the deal?: I wish I knew! Jo was smart and funny and sweet, but she was intensely secretive and shy, and never let anyone in. I loved her as a friend, and also had a crush on her- or at least the version of herself she let me see. We had a lot of fun together, and- though she never knew about it- she helped me get over my tactile sensitivty during our many projects together in drama class. I guess I kept a lot of things from her, too.

What went wrong?: Communication, mostly. After a long time, we finally revealed that we were interested in each other, and talked about dating. Then she stopped talking to me for no apparent reason. If I had to guess, I’d say it was self-sabotage due to a fear of rejection. At the time I was stymied and deeply hurt. I cared about her friendship more than the possibility of dating her, and it was her friendship I missed the most.

The lesson learned: It’s fun to be attracted to someone who’s enigmatic and mysterious, but if they don’t drop the act at some point, there’s something going on underneath that you probably don’t want to get drawn into.

Skye Jessel: 2003-2004

What was the deal?: Skye was my first real-life girlfriend. We had a couple of classes together, and though we were both put off by each other initially, we ended up talking to each other and found we had a lot in common. She had Asperger’s too, and was more or less my introduction to what female Aspies look and act like. In many ways she was typical: immaculately dressed, tightly wound, eager to please, simultaneously strong-willed and fragile. My fondness for She-Aspies starts here. Skye and I dated for precisely five weeks, though for the last week or so we weren’t on speaking terms.

What went wrong?: You’ve got two sixteen-year-old autistics with next to no dating experience. God, what could possibly go wrong? It was like a fire in a fireworks factory. Communication was the biggest problem. Both of us expected the other to be a mind-reader, and neither of us even tried to talk about our expectations or concerns, probably out of fear of rejection. Resentment piled up high and fast. Both of us wanted very much to be in a relationship, and were attracted to ideas we had about dating, and ideas we had about each other. But none of these ideas were based in reality. Oh, and I was also experiencing my first episode of seasonal affective disorder while we were dating. So I spent most of our relationship feeling panicky, sad, and undesirable. It was not fun.

The lesson learned: Talk to each other, and keep talking. Make sure you’re attracted to a person instead of an idea. Make sure they accept you for who you are, and accept them as well.

Jane Sutherland: 2010-2011

What was the deal?: After the double punch of losing both Joanna and Skye in the same year, I lost all interest in dating for the rest of high school. Then I got to university and got distracted and when I got settled into a routine I found that I didn’t really miss dating. Six years later, I met Jane in a social group at university. Jane was another She-Aspie, smart and well-put-together, quiet and decent, though she didn’t suffer fools gladly. I was much shyer than I’d been when I was younger, probably because I’d spent so much time alone in the interim, and was even hesitant to ask Jane to hang out platonically. We did a few times, and had fun, and I finally got up the courage to ask her out on a date. She thought about it for two days, then said no.

What went wrong?: Jane was a private, secretive person who kept to herself, and so I didn’t know- hardly anyone knew- that she was suffering from serious health problems. She was interested in me, but wasn’t at all in a position where she could date. In retrospect, I suppose she felt like a grenade. A few weeks after I asked her out, her health suddenly deterioriated and she almost died. I was one of the few people she allowed to come visit her in the hospital. Most people didn’t even know she was in the hospital. After Jane recovered, she stopped talking to me for reasons I never understood.

The lesson learned: Everyone’s fighting their own private battles, and no matter how much you care about a person, they’re not always going to want you around as a witness or cheerleader. And don’t even try to fight people’s battles for them. That’s a no-win scenario. You aren’t going to rescue anyone.

Amy Tomlinson: 2012-2013

What was the deal?: A year and a half after Jane and I stopped hanging out, I was horribly alone and lonely and so I decided to do something undignified and embarrassing and uncharacteristic: I signed up for OKCupid. It worked better than I’d ever imagined. A month after signing up, I happened upon a person I already basically knew: we’d been in the same program at university, though she was a doctoral student and I’d dropped out halfway through undergrad. Not only did we know some of the same people, but we’d been to some of the same parties. So we started hanging out, and got along famously. Amy is like a cartoon character: energetic, charismatic, friendly and fun. Right from the first time we met we were able to talk to each other about anything for hours. In some ways she reminded me of Naomi, which I took to be a good sign. Amy and I casually dated for a couple of months.

What went wrong?: Nothing, really. Even though we were seeing each other, we didn’t actually see much of each other. It turned out we wanted different things. I was looking for a serious relationship, and Amy wasn’t in a place where she could do that. This was because a lot of stuff in her life was on fire. So we talked about it, and decided we were better off just being friends. Then, in the very same conversation, Amy told me she had this friend named Hannah who wanted to meet me, and would I be interested in meeting her? I said yeah, what the hell.

The lesson learned: I’d always thought I was kind of bad at the whole dating thing, especially since three of the people I had been interested in abruptly and permanently stopped talking to me. Amy- who had much more dating experience than me- reassured me that I wasn’t the fuck-up I thought I was. And that meant a lot. She built up my confidence, which allowed me to move forward into a successful long-term relationship.