Date-tastrophy: The disastrous dates of an empath

Content warning: Includes discussion of sexual assault

When it comes to dating, I hate meeting people in public. I’m that girl who reaches for my drink and accidentally flings it across the room, inadvertently vaporizing it into a million shards, directly on the table of the crush I’ve been eyeing all night. He hasn’t looked at me once, but my vanity says “Oh yeah… you know I’m here and hot to trot.” I’ve always been a weirdo, and bitterly honest. My answer “What do you like to do?” is generally “Well, I like bugs, skeletons, and judging people by their dog’s breed.” You know, like when a guy’s a 10, but he owns a miniature poodle. Gross. My friend decided that I would do better not meeting people in person, so she signed me up for internet dating. I didn’t have a lot of responses to my account. I’m not being modest. Maybe because my usernames were things like “SpecialK911,” which really says “I do special K and will get it to you as fast as 911.” I also tried “Thenotbeardedlady.” Nothing says you’re actually a bearded lady more clearly than saying you’re not a bearded lady. It’s no wonder that when the messages did trickle in, I found, shall we say, some interesting people.


I have many regrets in my dating history. One of the first was dating a guy who actually had “King Slayer” as part of his Facebook name. However, he was no Jamie Lannister. On our first date, we had dinner and drinks, and then headed back to his place to hang out for a bit. The apartment was pristine, with the usual hipster decor: a typewriter on the wall, vintage furniture, copper mugs. It was minimalist chic with an industrial feel. The Kingslayer made me a classic olive martini, and then a Moscow mule in one of the aforementioned copper mugs. The night played out in a way unbefitting to a lady of high caliber, who I am not. Let’s just say I saw a Red Hot Chilli Peppers tattoo I didn’t know existed, and I would have rather been under that bridge.

A few weeks later I met another nice man from the internet. We had dinner and drinks, and once again I decided to hang out with him at his apartment. From every step I took – parking in the lot, walking in the door, walking up that spiral staircase, and seeing an all too familiar typewriter on the wall – I thought: Holy Crud. They’re roommates. Sure enough, Hipster Number Two made me a classic olive martini, and then a Moscow mule in a copper mug, and for purely scientific purposes, we snogged a little. It was not good. A second later, the Kingslayer walked in, and I got out of there like Usain Bolt running from a caffeinated cheetah. I never visited the Kingslayer, or his court jester again.

I love grabbing a drink on a first date. Just one. I like to feel relaxed, but not sloppy. And when it’s just one, there’s the added benefit of getting to bail fairly quickly. One time, I went on a bar date with a very handsome gentleman. He did so many interesting things, and good golly – I’m a sucker for tattoos. About half an hour into the date, around the time you’re learning who has pets and debating whether Wright’s or Blackbird Farm has the best ice cream, this guy dropped a down-right doozy on me: He said, “My dad was murdered and left in a dumpster.”

Immediately, my empathy bulldozed me. I didn’t end the date. I listened compassionately and intently to everything he said. I also stayed because darn it, I’m also a sucker for a good story. At the end of the date we parted ways. Here’s the part that gets a little sticky. I was a new comedian at the time, writing about my dates. I should have excluded this one, but I didn’t. In my ego, vanity, and delusion, I wrote what I thought was a killer joke. No pun intended. I figured he’d never know and everything would be fine.

A few weeks later I ran into this man at a festival. He asked if I wanted to join him for a drink, and I accepted. We watched a band for a minute and I saw a girl make eye contact with him, then quickly book it out of there. He volunteered that she was an ex, and that she had a restraining order on him. He actually said the words “not for rape, just the precursor.” Human me was terrified, but comedian me couldn’t have been more delighted for the delicious gems of material coming out of his mouth.

Much to my surprise, the next thing he said was, “I’m sorry I told you about my dad on a first date.” I said not to worry about it, and then my no filter mouth said, “Don’t worry, I kind of wrote a joke about it.” Then he asked to hear it. I’ve never felt so much chagrin at telling a joke, but I felt that if I had the guts to write it, he deserved to hear it. I started the joke: “I went on a date with a guy who had a deadbeat dad…” Let’s just say I made a grown man cry that day. But I’ll never forget the phrase “not for rape, just the precursor,” and when I think of that, I feel a little less badly about his tears.

So, there you have it folks. Those are two of a bucketful of internet dating stories where people divulge their innermost secrets to me. I’d say it doesn’t happen often, but strangers do it every day, everywhere I go, at any store, no matter what I’m wearing. I dated off the internet for three years and then finally quit. I hated talking to people forever, only to find out our chemistry was terrible. I hated the rollercoaster of emotions it brought about. I quit dating and pursued comedy full-time and six months later I met my husband through comedy. He is my second boyfriend. If you’re keeping track, that’s two boyfriends and two marriages. My husband is also a comedian, a podcaster, and the most genuine person I’ve ever met. He is my person. We met at an open mic – the place jokes go to die – and we found our own laughter.