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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Kat’s Adventures in Dating: The Absurd One

The Cabaret show flyer

I’ve decided to document some of my most memorable moments in dating, per a friend’s request. I’ve changed the names and am reusing the same five or six names, partly to hide people’s identities but also partly because I can’t remember half of their names anymore anyway. I hope you’ll find them as entertaining or interesting as I do… now that I’m past them.

John and I were talking exclusively on a dating app – we hadn’t exchanged phone numbers yet. But our chatting was going well and he threw me the hottest line a man can ever send me, on a dating app or otherwise:

“I have tickets to a show on Saturday night at 7pm. Wanna join?” 

SWOON.

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