Kat’s Adventures in Dating: The Worst Date That Turned Into the Best Date

dining room table

One thing that I still have not mastered even after 25 or more years of dating is trusting my gut and saying NO, loudly, and forcefully, when I need to. I’ve agreed to dates that made me uncomfortable with men I felt iffy about. I’ve continued on dates that weren’t serving me in any way, and then just felt worse when I had to find a way to excuse myself from the event without incurring the man’s wrath or ire by informing them that they are, in fact, the worst. 

There are times when you just feel meh about a person, and that’s ok. Or you’re not ready to date and so you’re just kinda’ lukewarm, even if the person is spectacular. And a good date will ask what’s up, and you’ll be able to communicate about it, and be genuinely open to hearing your opinion and your needs, and you’ll go your separate ways, and feelings will be hurt, but you were honest and everyone is better off. 

But there are times when a guy is objectively terrible in a number of ways, and there is no way to convey this, because when a guy is objectively terrible, he is generally not open to constructive criticism. This sucks, because it means he’s just going to continue to be objectively terrible. 

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Kat’s Adventures in Dating: Misadventures in Feminism

Photo by chloe s. on Unsplash

I am an unabashed feminist. I have been my whole life. It’s probably genetic, and it’s definitely not something I’ve ever felt ashamed of. I tend to gravitate towards people who feel similarly in my dating life (because otherwise someone would probably end up murdered), but there have been times when my outspoken feminism has made things… funny. 

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Kat’s Adventures in Dating: Valentine’s Day Edition

I do not hide the fact that I think Valentine’s Day is the best. I know, it’s an unpopular opinion. Whatever. 

The one thing about Valentine’s Day that can suck for everyone is ambiguity. If you’re just sort of dating someone or in a situationship, it can be hard to determine expectations or boundaries. I really appreciate bravery and trying, and I respect people who put themselves out there even if they’re not sure what the response is going to be – not just on Valentine’s Day, but in life. It’s worth it, I think. 

So I thought I’d share some really excellent Valentines that missed the mark – not because they didn’t try, but because I wasn’t in the same place they were.

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Kat’s Adventures in Dating: The 6 out of 10

Five stars

I met Gary on OKCupid when I was living in Albuquerque. He was a pharmacist and a bodybuilder, and one of my friends knew him. 

“He’s got a real thick South Valley accent,” she told me, “but other than that, he’s cool.” 

We chatted back and forth on Google Chat for a while and went out on a date – dinner and drinks, probably. We had some chemistry but didn’t kiss goodnight. He even brought up his accent.

“I sound like a real mocho,” he said. 

(He did. I’m fine with accents. Generally like them, in fact.) 

I invited him to come to a movie at the Southwest Gay and Lesbian Film Fest with me, since I’d gotten free passes. He agreed.

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Kat’s Adventures in Dating: The Failures to Launch

As a veteran of the online dating scene, I am fully subscribed to the idea that you should meet in person as soon as you are able (and comfortable enough) to do so. A lot of my friends will spend weeks texting with someone on the app, not exchanging phone numbers or even last names, before they feel comfortable enough to set a time and date and see someone’s face in real life. This is, to me, the death of all possible chemistry. If we can’t meet within about a week of matching, it’s just never gonna’ work for me.

Every once in a while, I’ll match with someone on a dating site and plan to meet them, but something will stop that meeting from happening. And often it’s something the guy has done that makes me really just not want to meet up with them. Here are a few examples.

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Kat’s Adventures in Dating: The Bernese Mountain Dog

A Bernese Mountain Dog

When I lived in northern New Jersey in my youth, I’d go into the City (that’s New York City, generally Manhattan, for anyone who has never lived in that metropolitan area) often for grad school classes or to see friends. The train schedules and bus schedules were made more for daytime commuters than nighttime revelers (or students), so I’d drive my little red Mazda Miata and find parking on the street in the West Village. I only got towed once, and I was never late to class because of parking, so I was pretty lucky.

One buzzy Friday night I got dolled up and went into town to visit Theo, a guy I’d been seeing for a few weeks. We had gone to the same high school but didn’t know each other until we were both living in/around NYC. He was a grad student in philosophy (you’re right, that should have been a red flag) and he was also very emotionally volatile which, well, I was too. I have always had this insufferable fantasy about falling in love with a “hometown boy” that I had everything in common with but had gotten out to see the world like me, so he scratched some funny itch. He was also tall with broad shoulders and nice eyes, which helped. 

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The Story So Far

When I was very young, I learned that I did not make anyone’s life better.

I don’t know where or how or from whom I learned this. There’s no “aha” moment in my memory that I can point to. It could have been the Southern Baptist Church’s teaching that you are literally worthless without God. Or just the small T “trauma” of growing up as a highly sensitive person in a house overrun by three girls under four years old (two of them twins!).

But somewhere along the line, I came upon the belief that not only did I not improve the lives of people I interacted with, but I actively made them worse.

This became more potent in my young adulthood, when I lost my faith (and thus the one thing that would render me not worthless), and felt like a major disappointment to my parents, and went to a college where I never really felt I fit in.

I never felt that I could be close to anyone, not really. I couldn’t be vulnerable. They’d hate me if they knew me. So I’d do things, unconsciously, to prove that they didn’t mean anything to me, because I knew I couldn’t mean anything to them. I would push people away, quietly usually, but sometimes loudly and irreparably, because I could not communicate the utter turmoil that was going on in my heart and lungs.

Then when I was 20 years old I fell in love with a man who had a terminal illness. And the first year we were together, he got better. Whereas, before me, he would normally need to be hospitalized every six months to take IV antibiotics, he didn’t need them for a full nine months after we got together. Suddenly, there was someone for whom life was actually better with me in it.

This was all an illusion of course; no one with a truly terminal illness “gets better”. The long march toward their death may be temporarily slowed or their symptoms alleviated briefly, but the terminality persists.

So when he went back to being sicker, a little switch in my brain said, “Ah, see, that wasn’t true. That was a fluke. You do not make his life better.”

And there I was again, engaging in self-sabotage as a maladapted method of self-protection. I was a cheater. I ran away. Even though I loved him more than breathing, I couldn’t handle it.

We split up.

And then when I was 24, my best friend hanged himself. Deep down I knew it was because he had developed schizophrenia. But the part of my brain that looked for the hurt I caused also made a list of how our relationship had changed in the year or two before he’d died. He’d hated me for cheating on my boyfriend. He’d hated that I was depressed when he was working so hard to get out of his own sadness. He’d stopped responding to my text messages. He’d quit asking if I might consider officiating his wedding.

These major events cemented in my mind that I was, in fact, worthless, unloveable, unwantable, and just a burden. There was proof! Fickle as that proof may be, it existed for me.

And because nothing is as isolating as grief, I was further isolated from any proof to the contrary.

In fact, every iota of my life became part of the proof: every job I left with my tail between my legs; every man I dated who stopped calling me back; every milestone I missed that my sisters attained with ease; all my losses and failures were my just deserts. It solidified the narrative further.

Ten years later, I met and married a man who actually told me I was “a nightmare”. He complained that I wasn’t fun; that I talked too much around other people and bored them; that I was getting fat because I had no self control, and that he “couldn’t help what he was attracted to”; that I slept too much; that I cared too much about money; that I needed to wear tighter clothing (even as he criticized the size that my body was becoming)…

Overall, he just let me know in ways big and small that I just wasn’t worth it. I wasn’t worth doing what he said he would do, from something as small as unloading the dishwasher to something as big as taking care of things for a day when I got out of surgery. I wasn’t worth being on time for. I wasn’t worth buying flowers for. I wasn’t worth listening to. I wasn’t worth therapy.

He had his own issues and his own insecurities, and those devolved into alcoholism and self destruction of his own. And I was not a nice person to him, because he had one job for me: further proof that I was worthless. When he fulfilled that purpose, I needed to get away from him, and the only way I knew to do that was by kicking and spitting and screaming.

But something was changing. The pandemic, probably, and the civil unrest around protests and politics all woke something inside of me. I started to do things to take care of me. I saw a nutritionist and got my weight under control. I started running more. I cashed in a retirement fund for a down payment on a house. I got a full-time job with good benefits and excellent pay so that I had some security. I took care of things.

So when he spent $600 on sex videos from cam girls and sex workers in the three weeks after my last major surgery and went back to drinking, I had an inkling of some flicker of self worth. I kicked him out. I filed for divorce. I let him stay on my insurance so he could go to rehab, and then I cut him off.

In the 10 months since I kicked him out, I’ve gone through an enormous transformation, mostly just of realization.

I see now that the quiet little tape recording of my worthlessness informs a lot of what I do or don’t do. It makes me anxious when I’m not invited to parties, rather than wondering if I actually like the people throwing the parties. It makes me seek out flaws in potential romantic partners so that I can justify dumping them, or to settle on those who can’t give me what I need so that I can fulfill the narrative of my own worthlessness. It makes me turn to comfort food when I am uncomfortable, rather than sitting with the feelings and finding ways to confront them. It makes me choose the escape of sleep rather than the reality of feeling joy at finishing the things I need to do.

As the seasons change and I deal with summing up a year that could serve as a very fine proofpoint of my worthlessness — a divorce (the only one in my family); weight gain; debt; endless dates with men I haven’t been interested in; a messy house that may or may not be falling apart; months of putting in the bare minimum at work and relationships — I am confronted with changing the narrative again.

I don’t quite have the tools to do it. I don’t know how to ask for help, either, because I don’t even know what I need. When people make suggestions, I resent them for criticizing me (even though they’re not; it’s just my worthlessness tape recording coming into play).

It may be that months of solitude are in order, although that’s an extreme that could do more damage than just sitting in the middle ground, grieving for my losses without assigning them as my own fault. There is no fault. There’s responsibility to deal with them, but that’s all.

And when I find myself listing the proof that everyone would be better off without me, I can just see the list for a moment. And maybe think it’s true. Or maybe just let it be another list, like the things I need to do today or the groceries I need to buy. Lists are meant for checking off and then moving on.

Sunday morning quarantine

A picture of my patio on a sunny day with plants, my notebook, a cup of tea, and a yellow watering can

I woke up at 8:30 and couldn’t sleep anymore. I scrolled through Facebook thinking, I’ll just let this pass and then I’ll go back to sleep for a few more hours. We’d gone to bed at 2am the night before, not for any reason, just watching the last season of “Schitt’s Creek” aimlessly after having binged “The Tiger King” before. I’d drifted off around 3am or so. Five hours is more sleep than most Americans with day jobs get, I thought. But it felt like a tragedy, the inability to sleep in on a Sunday.

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